Chester, VT, United States Accommodations

Accommodations in Chester

Home/Apartment
5br Home/Apartment
  • Wifi
  • Parking
The SpaceOur house is located in the charming town of Chester within walking distance of shops and restaurants and an art gallery. It is very large with a beautiful wet bar, pellet stove and fireplace. Decorated with antiques and vintage furnishings, it is a comfortable space for a group of friends or family. We also have a port crib/pack and play for children under 30 pounds. Guest AccessFull kitchen, 4 full baths, wet bar loaded with glassware, High speed Internet, Direct TV, snow shoes, sleds and other winter items. Outside games for summer including bocce and corn hole, along with a new gas grill. Loads of board games too! There is also a port crib for a child up to 30 pounds. Interaction with GuestsWe are always available during a guest's stay to answer any questions by phone or email. The NeighborhoodThe town of Chester is a beautiful Vermont village. We are located by the library and near the green where there are restaurants and shops, including a fe new antique shops. We also are located close to McLomain's Scottish Pub and the Pizza Stone. Chester has a town pool and great sleigh riding hill and is a lovely place to stroll and cross over the hanging bridge on the Williams Rver! Getting AroundOur driveway has plenty of parking and one can easily walk to any establishments in town.
Home/Apartment
5br Home/Apartment
  • Wifi
  • Parking
The SpaceCharming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of parking besides). This house was built between 1800 and 1805, it is NOT modernized (we like it this way!), but is very cozy and well-equipped. The two living rooms each have very well-built fireplaces; wood is included. We supply all sheets, towels, and everything you'll need in the kitchen. For skiiers, Magic Mountain and Okemo are under 14 miles away. Bromley, Stratton, Killington, Mt Snow, and Pico are all between 20 and 40 miles away. Grafton Pond Park is under 9 miles away and has snow tubing and great cross-country trails. We're within walking distance of the delightful town of Chester. There are cute shops, several terrific tavern-style restaurants with great food, a beautiful bakery, and, in Ludlow, the next town north (where Okemo is), there are tons more restaurants, including one of our very favorite restaurants anywhere, Downtown Grocery. We're close to multi-dealer Stone House Antiques and several other antique shops. Also 7-1/2 miles to the (in)famous Vermont Country Store. There are frequent festivals and seasonal events in the area. The house is on a well-traveled road and very easy to get to. We're a little over 2-1/2 hours from Boston, and a little under 4 hours from NY, ten miles off of route 91. Amtrak stops in Bellows Falls, 15 miles away. We have flat screen TV, cable, wireless, and a great old-fashioned game table. (We also have a collection of games that are pre-plastic. :) We rent all times of year. Rates are $175/weekday night, $200/weekend night, $1100/week, $3300/month. VT rooms tax is an additional 9% (this in included in your price quote), but this does not apply to stays over 30 days. Rates are lower during spring and summer, please inquire. A security deposit and cleaning fee are required. We do permit pets but there is an additional cleaning fee, and no more than two pets at a time are permitted. Guest AccessNothing is off limits, although the barn is at your own risk. Interaction with GuestsWe may not see you at all. Or we may see you when you check in and/or when you leave. Of course you can phone or text us anytime! The NeighborhoodIt is a charming old "painted" town, walking distance to lots of shops, bakeries, restaurants, pubs, a historical society, and there are frequently community fairs and festivals. Close to lots of ski areas, lakes, antique shops, golf courses, and skeet- and trap-shooting down the road. Getting AroundWe are on route 11, just west of the town of Chester. You can walk in to town, and to the town pool and the VAST snowmobile/mountain bike trails. We are ten miles west of VT exit 5 off route 91. Amtrak has a stop in Bellows Falls, about 15 miles away.
Bedroom
Bedroom
  • Wifi
  • Breakfast
  • Parking
The SpaceBeautiful 1780 colonial B&B on the green near.Okemo Ski area 7 guest rooms from $129 to $209 see Chester House Inn Guest AccessTV in room Interaction with GuestsArrivel and Breakfast The NeighborhoodQuiet Getting AroundShuttel to Okemo
b&b
6br b&b
    This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe. We are located on the Main street in the center of Chester, Vermont, on the green. Chester is a very beautiful quintessential Vermont town setting with shops, bookstore, galleries, restaurants across the street on the green and within walking distance. Close by: skiing, golfing, swimming, hiking, biking, wildlife, museums, theater, music and more. About Chester - The Misty Valley Chester is a small Vermont village nestled in the Eastern slopes of the Green Mountains in the Williams River Valley, along the South Central tier of the state. Our citizenry is not as diverse as some places but we do have a fine mix of natives and those from away - some from far, far away who have happily decided to make Chester their home too. Our population is small compared to our landmass -- around 3,000 residents within 56 square miles, which can make for a solitude not found in a city. And our land offers some of the most diverse and beautiful landscapes imaginable. You'll never grow tired of experiencing our hills and mountains, valleys and streams, rocky ledges and pastures. In all seasons, Chester is a wonder to behold. The three branches of the Williams River come together in downtown Chester as they head through Rockingham to the Connecticut River. The North Branch begins in Andover, runs through Ludlow then turns south along Route 103 through the Stone Village. The South Branch runs from Tater Hill Golf Course along Popple Dungeon Road before turning north at the Grafton Road. And the Middle Branch runs from Andover to Chester along Route 11. There are numerous spots for fishing or dipping along each branch. Because of the way that Chester sits along these branches and the various mountains that divide it, our weather patterns between areas can be almost as diverse as our landscape. Popple Dungeon may be getting hit with a snowstorm while Main Street is sunny -- or vise versa. What definitely happens in this area is morning mists rolling off the mountains. Two Historic Districts The town is comprised of two districts in the National Register of Historic Places: The Stone Village Historic District (also known as the Stone Houses at Chester Depot) are on both sides of Route 103 North. It consists of 10 Greek Revival buildings that also includes a former school (now a home) and a Unitarian Universalist Church. This district was recognized in 1974. The Chester Village Historic District, also known as South Village, was recognized in 1985. It is roughly bounded by Lovers Lane Brook, Maple Street, the Middle Branch of the Williams River and Lovers Lane. Its historic significance is its mix of Late Victorian, Colonial Revival and Federal style architecture. These homes, houses of worship and businesses were built between 1750 and 1924. Currently, there are 40 Historic Districts in Vermont. Here are a few numbers you should know: Chester has 1. Zero stoplights 2. One ZIP code -- 05143 3.Two gas stations 4. One phone exchange -- 875 (Vermont only has one Area Code -- 802).
    b&b
    1br b&b
      The Tower Room in Hugging Bear Inn and Shoppe, a bed 'n breakfast Inn. Cozy and romantic with queen-sized bed, full private bathroom with shower and air-conditioning for hot weather days. A round room (actually hexagonal) in the tower of this Victorian home overlooks the village green. Full Vermont breakfast made to order every morning. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our other listing for renting the entire Hugging Bear Inn. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe. We are located on the Main street in the center of Chester, Vermont, on the green. Chester is a very beautiful quintessential Vermont town setting with shops, bookstore, galleries, restaurants across the street on the green and within walking distance. Close by: skiing, golfing, swimming, hiking, biking, wildlife, museums, theater, music and more. About Chester - The Misty Valley Chester is a small Vermont village nestled in the Eastern slopes of the Green Mountains in the Williams River Valley, along the South Central tier of the state. Our citizenry is not as diverse as some places but we do have a fine mix of natives and those from away - some from far, far away who have happily decided to make Chester their home too. Our population is small compared to our landmass -- around 3,000 residents within 56 square miles, which can make for a solitude not found in a city. And our land offers some of the most diverse and beautiful landscapes imaginable. You'll never grow tired of experiencing our hills and mountains, valleys and streams, rocky ledges and pastures. In all seasons, Chester is a wonder to behold. The three branches of the Williams River come together in downtown Chester as they head through Rockingham to the Connecticut River. The North Branch begins in Andover, runs through Ludlow then turns south along Route 103 through the Stone Village. The South Branch runs from Tater Hill Golf Course along Popple Dungeon Road before turning north at the Grafton Road. And the Middle Branch runs from Andover to Chester along Route 11. There are numerous spots for fishing or dipping along each branch. Because of the way that Chester sits along these branches and the various mountains that divide it, our weather patterns between areas can be almost as diverse as our landscape. Popple Dungeon may be getting hit with a snowstorm while Main Street is sunny -- or vise versa. What definitely happens in this area is morning mists rolling off the mountains. Two Historic Districts The town is comprised of two districts in the National Register of Historic Places: The Stone Village Historic District (also known as the Stone Houses at Chester Depot) are on both sides of Route 103 North. It consists of 10 Greek Revival buildings that also includes a former school (now a home) and a Unitarian Universalist Church. This district was recognized in 1974. The Chester Village Historic District, also known as South Village, was recognized in 1985. It is roughly bounded by Lovers Lane Brook, Maple Street, the Middle Branch of the Williams River and Lovers Lane. Its historic significance is its mix of Late Victorian, Colonial Revival and Federal style architecture. These homes, houses of worship and businesses were built between 1750 and 1924. Currently, there are 40 Historic Districts in Vermont. Here are a few numbers you should know: Chester has 1. Zero stoplights 2. One ZIP code -- 05143 3.Two gas stations 4. One phone exchange -- 875 (Vermont only has one Area Code -- 802).
      b&b
      1br b&b
        Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. Also features a infrared fireplace heater. Full Vermont breakfast made to order every morning. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our other listing for renting the entire Hugging Bear Inn. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe. We are located on the Main street in the center of Chester, Vermont, on the green. Chester is a very beautiful quintessential Vermont town setting with shops, bookstore, galleries, restaurants across the street on the green and within walking distance. Close by: skiing, golfing, swimming, hiking, biking, wildlife, museums, theater, music and more. About Chester - The Misty Valley Chester is a small Vermont village nestled in the Eastern slopes of the Green Mountains in the Williams River Valley, along the South Central tier of the state. Our citizenry is not as diverse as some places but we do have a fine mix of natives and those from away - some from far, far away who have happily decided to make Chester their home too. Our population is small compared to our landmass -- around 3,000 residents within 56 square miles, which can make for a solitude not found in a city. And our land offers some of the most diverse and beautiful landscapes imaginable. You'll never grow tired of experiencing our hills and mountains, valleys and streams, rocky ledges and pastures. In all seasons, Chester is a wonder to behold. The three branches of the Williams River come together in downtown Chester as they head through Rockingham to the Connecticut River. The North Branch begins in Andover, runs through Ludlow then turns south along Route 103 through the Stone Village. The South Branch runs from Tater Hill Golf Course along Popple Dungeon Road before turning north at the Grafton Road. And the Middle Branch runs from Andover to Chester along Route 11. There are numerous spots for fishing or dipping along each branch. Because of the way that Chester sits along these branches and the various mountains that divide it, our weather patterns between areas can be almost as diverse as our landscape. Popple Dungeon may be getting hit with a snowstorm while Main Street is sunny -- or vise versa. What definitely happens in this area is morning mists rolling off the mountains. Two Historic Districts The town is comprised of two districts in the National Register of Historic Places: The Stone Village Historic District (also known as the Stone Houses at Chester Depot) are on both sides of Route 103 North. It consists of 10 Greek Revival buildings that also includes a former school (now a home) and a Unitarian Universalist Church. This district was recognized in 1974. The Chester Village Historic District, also known as South Village, was recognized in 1985. It is roughly bounded by Lovers Lane Brook, Maple Street, the Middle Branch of the Williams River and Lovers Lane. Its historic significance is its mix of Late Victorian, Colonial Revival and Federal style architecture. These homes, houses of worship and businesses were built between 1750 and 1924. Currently, there are 40 Historic Districts in Vermont. Here are a few numbers you should know: Chester has 1. Zero stoplights 2. One ZIP code -- 05143 3.Two gas stations 4. One phone exchange -- 875 (Vermont only has one Area Code -- 802).
        b&b
        1br b&b
          A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our other listing for renting the entire Hugging Bear Inn. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition. It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe. We are located on the Main street in the center of Chester, VT, on the green. Chester is a very beautiful quintessential Vermont town setting with shops, bookstore, galleries, restaurants across the street on the green and within walking distance. Close by: skiing, golfing, swimming, hiking, biking, wildlife, museums, theater, music and more. About Chester - The Misty Valley Chester is a small Vermont village nestled in the Eastern slopes of the Green Mountains in the Williams River Valley, along the South Central tier of the state. Our citizenry is not as diverse as some places but we do have a fine mix of natives and those from away - some from far, far away who have happily decided to make Chester their home too. Our population is small compared to our landmass -- around 3,000 residents within 56 square miles, which can make for a solitude not found in a city. And our land offers some of the most diverse and beautiful landscapes imaginable. You'll never grow tired of experiencing our hills and mountains, valleys and streams, rocky ledges and pastures. In all seasons, Chester is a wonder to behold. The three branches of the Williams River come together in downtown Chester as they head through Rockingham to the Connecticut River. The North Branch begins in Andover, runs through Ludlow then turns south along Route 103 through the Stone Village. The South Branch runs from Tater Hill Golf Course along Popple Dungeon Road before turning north at the Grafton Road. And the Middle Branch runs from Andover to Chester along Route 11. There are numerous spots for fishing or dipping along each branch. Because of the way that Chester sits along these branches and the various mountains that divide it, our weather patterns between areas can be almost as diverse as our landscape. Popple Dungeon may be getting hit with a snowstorm while Main Street is sunny -- or vise versa. What definitely happens in this area is morning mists rolling off the mountains. Two Historic Districts The town is comprised of two districts in the National Register of Historic Places: The Stone Village Historic District (also known as the Stone Houses at Chester Depot) are on both sides of Route 103 North. It consists of 10 Greek Revival buildings that also includes a former school (now a home) and a Unitarian Universalist Church. This district was recognized in 1974. The Chester Village Historic District, also known as South Village, was recognized in 1985. It is roughly bounded by Lovers Lane Brook, Maple Street, the Middle Branch of the Williams River and Lovers Lane. Its historic significance is its mix of Late Victorian, Colonial Revival and Federal style architecture. These homes, houses of worship and businesses were built between 1750 and 1924. Currently, there are 40 Historic Districts in Vermont. Here are a few numbers you should know: Chester has 1. Zero stoplights 2. One ZIP code -- 05143 3.Two gas stations 4. One phone exchange -- 875 (Vermont only has one Area Code -- 802).
          house
          5br house
          • Pets Allowed
          Charming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of parking besides). This house was built between 1800 and 1805, it is NOT modernized (we like it this way!), but is very cozy and well-equipped. The two living rooms each have very well-built fireplaces; wood is included. We supply all sheets, towels, and everything you'll need in the kitchen. We have flat screen TV, cable, wireless, and a great old-fashioned game table. (We also have a collection of games that are pre-plastic. :) The house is available now. We rent all times of year. We have a two-night minimum but much prefer to rent by the week or month. A security deposit and cleaning fee are required. Vermont tax is 9%. We do permit pets but there is an additional cleaning fee, and no more than two pets at a time are permitted. Beds: 1 King Bed, 1 Queen Bed, 6 Twin Beds Lodging tax: 9 Deposits: $300 security/damage deposit Payment Options: Cashier's Check, Money Order, PayPal, Personal Check Other Fees: $150 cleaning fee $50/pet, no more than two pets. No VT state tax for stays of more than 30 days with a lease. Charming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of parking besides). This house was built between 1800 and 1805, it is NOT modernized (we like it this way!), but is very cozy and well-equipped. The two living rooms each have very well-built fireplaces; wood is included. We supply all sheets, towels, and everything you'll need in the kitchen. We have flat screen TV, cable, wireless, and a great old-fashioned game table. (We also have a collection of games that are pre-plastic. :) The house is available now. We rent all times of year. We have a two-night minimum but much prefer to rent by the week or month. A security deposit and cleaning fee are required. Vermont tax is 9%. We do permit pets but there is an additional cleaning fee, and no more than two pets at a time are permitted. Beds: 1 King Bed, 1 Queen Bed, 6 Twin Beds
          Home/Apartment
          3br Home/Apartment
          • Wifi
          • Parking
          The SpaceOur 3 bedroom and 2 bathroom house is spacious enough for 1-2 families or 2-3 couples (enough room for 8 guests) to enjoy! A beautiful antique Stone House in Historic Chester Village! Enjoy a sidewalk stroll down the street to picturesque Chester Village. Buildings from yesteryear house restaurants, antique shops, a book store, a yoga studio, an organic grocery store, bakery, and numerous quaint gift and clothing shops. IN THE WINTER, there is so much to do in Vermont! A short walk from the house is a great sledding hill for visitors of all ages (there are 2 sleds at the house for use). The sledding hill was a former J-rope ski lift back in the 1970’s. Also near the sledding hill, visitors can snow shoe for miles on the VAST trails. An evening stroll to any of the local restaurants or pubs is always fun (especially when it is snowing out!) In addition, our house is located close to the ski resorts -Okemo, Magic, Bromley and Stratton. Each resort has a host of their own outdoor activities including ice skating, snow shoeing and tubing. A 20 minute drive brings you to Grafton Ponds where cross country skis can be rented and used on their track or mountain. Cozy up with some hot chocolate at their warming house or head out tubing on their hillside. There is lots to do in the area! Stroll the sidewalks to visit Chester Village’s quaint gift shops, antique shops, art galleries and restaurants. It’s a short walk along picturesque sidewalks to the Chester Recreation Area, too. There you will find a gazebo, play scape, tennis and basketball courts, soccer and baseball fields and a skate board park. Visit the 2 maple sugar houses in Chester to see how maple syrup is made. Hike or bike on the local trails. Walk to the Baba Louis Bakery for some fresh bread, pastry or lunch. Swing the clubs at Okemo’s Tater Hill Golf Course. Or relax and enjoy local spa services. Our 1843 Stone House has all the charm that you’d expect from an antique Vermont home. It has all the modern amenities to make your stay comfortable and cozy. Visitors are greeted with completely redecorated living spaces. A welcoming screened-in porch that leads into a multipurpose mudroom. The mudroom has ample storage for ski and snow gear or a place to kick up your feet and relax. A well-stocked kitchen and spacious dining area has seating for 8. Lounge in the family room where board games, TV watching and relaxing can be enjoyed. In the autumn and winter, cozy up to the propane (log burning) stove for the evening. Also, in the cooler weather, the main stone house is heated with forced hot air and the mudroom has a separate Renai propane space heater. Bedroom #1 – 1st floor- 1 Queen bed with an attached en suite (3/4 bath). This bedroom has a non working fireplace. Bedroom #2 – 2nd floor- (total of 4 beds) 2 twin beds, 1 twin trundle pull out bed and 1 full bed Bedroom #3 – 2nd floor- 1 Queen bed First Floor - 3/4 bath (toilet, sink and walk in shower) Second Floor - Full bath (toilet, sink and tub/shower combination) The amenities include laundry on the first floor and wireless internet provided for those who would like to stay connected to the outside world. Verizon and AT&T have great reception at the house. The yard is spacious and provides additional outdoor space for dining, relaxing and star gazing by the fire pit. The house is on a well-traveled road and in a location that is easily accessible. IN THE WINTER, grab a sled and walk to the Chester Recreation area and enjoy the best sledding hill around – formerly known as the Pinnacle ski area! When you tire of sledding, strap on some snow shoes or drive your snow mobile and head out on the VAST trail. It's located adjacent to the Recreation area. Cross country ski, snow shoe or tube at Grafton Pond. Ice skate at Jackson Gore's outdoor covered arena. Enjoy a sleigh ride at the Billings Farm. The fun doesn’t end there, enjoy some family time at the town maintained ice skating rink. Enjoy your day skiing at a local mountain: located approximately a 20 minute drive to Okemo and 15 minutes to Magic and 25 minutes to Stratton and Bromley. Come and enjoy Vermont from our home! Guest AccessGuests can enjoy full use of the our 1843 stone house, yard and garage except (1) locked pantry and the locked loft area above the garage. We ask that the basement be accessed for emergencies only. The house is accessible using a key code system. (No keys are necessary). Interaction with GuestsWe are available via phone, text and email during your stay. We are always happy to help you or offer recommendations. Please let us know early on if you are experiencing any problems so that we can rectify issues so that you can relax and enjoy your vacation. The NeighborhoodOur neighborhood is full of antique homes each with its own uniqueness, history and beauty. A short stroll on the sidewalk leads to the Historic Chester Green where shops and restaurants can be enjoyed. The house is in a historic district with neighbors on each side. Sidewalks into town adorn the road. The road is well traveled and the speed limit by the house and through Chester Village is enforced at 25 mph. Getting AroundParking for 3 cars in our driveway and 1 car in the garage. Other Things to NoteOkemo and Magic Montain are 20 minutes away. Bromley and Stratton are 25 minutes away. Killlington is 45 minutes away. Lake Lowell is under 15 minutes. Manchester Tanger outlets are 35 minutes away. VAST snowmobile Trail access is 1 mile. Grafton Ponds is 20 minutes. Multiple restaurants within walking distance. Bank, gas station and convenience store all within 1 mile.
          Bedroom
          Bedroom
          • Wifi
          • Breakfast
          • Parking
          The SpaceNewly renovated in 2015, The Karass Inn offers comfortable, simply appointed rooms and a relaxed, intimate atmosphere. Each of our rooms have been lovingly decorated with an eye towards simplicity and sustainability. Our cozy queen rooms feature pillow top mattresses, cushy upholstered headboards, a small seating area with table, and restored antique furniture. This room has an adjoining private bathroom with shower. Guest AccessYou're welcome to hang out in our great room and share (complimentary hot) breakfast with us in our dining room. Getting AroundPark for free in our private lot. Shuttle service to and from Bellows Falls train and bus stations is a possibility (for a fee)- please contact us for details. Other Things to NoteYour room rate includes a 9% Vermont Meals & Rooms tax.
          Bedroom
          Bedroom
          • Wifi
          • Breakfast
          • Parking
          The SpaceNewly renovated in 2015, The Karass Inn offers comfortable, simply appointed rooms and a relaxed, intimate atmosphere. Each of our rooms have been lovingly decorated with an eye towards simplicity and sustainability. Our cozy rooms feature pillow top mattresses, cushy upholstered headboards, and restored antique furniture. This room has an adjoining private bathroom with shower. Guest AccessYou're welcome to hang out in our great room and share (complimentary hot) breakfast with us in our dining room. Getting AroundPark for free in our private lot. Shuttle service to and from Bellows Falls train and bus stations is a possibility (for a fee)- please contact us for details. Other Things to NoteYour room rate includes a 9% Vermont Meals & Rooms tax.
          Home/Apartment
          2br Home/Apartment
          • Pets Allowed
          • Parking
          Our brick cape cod style home is 17 miles from Okemo Mountain Resort, 25 miles from Bromley Mountain Ski Resort, 16 miles from Magic Mountain Ski Area, 4 miles from the Vermont Country Store and historic downtown Chester VT.
          Bedroom
          Bedroom
          • Wifi
          • Breakfast
          • Parking
          The SpaceNewly renovated in 2015, The Karass Inn offers comfortable, simply appointed rooms and a relaxed, intimate atmosphere. Each of our rooms have been lovingly decorated with an eye towards simplicity and sustainability. Our cozy queen rooms feature pillow top mattresses, cushy upholstered headboards, a small seating area with table, and restored antique furniture. This room has an adjoining private bathroom with shower. Guest AccessYou're welcome to hang out in our great room and share (complimentary hot) breakfast with us in our dining room. Getting AroundPark for free in our private lot. Shuttle service to and from Bellows Falls train and bus stations is a possibility (for a fee)- please contact us for details. Other Things to NoteYour room rate includes a 9% Vermont Meals & Rooms tax.
          Bedroom
          Bedroom
          • Wifi
          • Breakfast
          • Parking
          The SpaceNewly renovated in 2015, The Karass Inn offers comfortable, simply appointed rooms and a relaxed, intimate atmosphere. Each of our rooms have been lovingly decorated with an eye towards simplicity and sustainability. Our cozy queen rooms feature pillow top mattresses, cushy upholstered headboards, a small seating area with table, and restored antique furniture. This room has an adjoining private bathroom with shower. Guest AccessYou're welcome to hang out in our great room and share (complimentary hot) breakfast with us in our dining room. Getting AroundPark for free in our private lot. Shuttle service to and from Bellows Falls train and bus stations is a possibility (for a fee)- please contact us for details. Other Things to NoteYour room rate includes a 9% Vermont Meals & Rooms tax.
          bed and breakfast
          5br bed and breakfast
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in Chester, this bed & breakfast is 0.2 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          inn
          20br inn
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          hotel
          12br hotel
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in Chester, this motel is 1.7 mi (2.7 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          hotel
          Poor
          26 reviews
          7br hotel
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          hotel
          13 reviews
          9br hotel
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in Chester, this bed & breakfast is 0.3 mi (0.5 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          hotel
          3br hotel
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in the mountains, this bed & breakfast is 0.2 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          Home/Apartment
          Excellent
          3 reviews
          2br Home/Apartment
          • Wifi
          • Pets Allowed
          • Parking
          The SpaceThis house sits on stilts above a soothing stream and waterfall. The sound of the waterfall is actually the first thing you notice when you open the car door. We have three semi-secluded acres off a dirt road that include woods, stream, waterfall, fire pit and cedar sauna which has skylights and a wood burning stove. There is also a deck, grill, garden, outdoor shower and, of course, a hammock. Inside there is a Jotul woodstove and a fireplace for chilly nights as well as a record player and plenty of board games and puzzles for rainy days. The main part of the house features an open kitchen and living room. There is a sleeping loft above the kitchen with a comfy queen size bed. The loft is accessed by a ladder. The other side of the house has a large bathroom with a claw foot tub and a cedar and soapstone shower with rain shower head. Upstairs there is a bedroom with a full size bed. This house is great for people who want to get away and be in nature but with some amenities. However, many of our friends like to call it "indoor camping" because it is not a conventional house and it is not hermetically sealed as some people may prefer. The glass wall of the house really blurs the line between the outdoor and indoor. We have the occasional critter - mouse or spider. It's loads of fun to be there but requires someone who appreciates being outside, chopping their own firewood and doesn't mind that the house is a little rough around the edges. We've been working on this house for 15 years and it still is (and will probably always be) a work in progress! Sorry - no kids (too dangerous) and pets on a case by case basis. Please note we do not have an oven, only a stove top. Also, the woodstove is the primary source of heat for the colder seasons. We have a canoe and a kayak which guests are welcome to use. There are many places within driving distance where you can launch. Feel free to contact us with any questions! Guest AccessEmail for more info Interaction with GuestsWe are usually in NYC when guests are here but are available 24/7 be email & phone. The NeighborhoodWe live on a dirt road near a covered bridge. There are plenty of farmstands nearby where you can buy fresh eggs & produce. Getting AroundA car is necessary.
          Home/Apartment
          1br Home/Apartment
          • Wifi
          • Breakfast
          • Parking
          The SpaceLocated 1.5mi. from the historical village of Grafton and all its amenities. The Woodshed is a clean, comfortable, very quiet and secluded loft apt., nestled in the foothills of the Green Mts. with direct access to 146 acres of Putnam State Forest's VAST trails for hiking and snowmobiles. There is a full size range, sm. fridge, coffee maker, toaster, wi-fi. darts and a refreshing outdoor shower as well as the indoor. Guest AccessAlso available are the sun deck and BBQ areas. Adjacent to the "Woodshed" is "Rocky Boy Post" a 24 Track Recording/rehearsal studio available for hire, for demos/mastering or live rehearsal. You can get more info and listen to sample audio (EMAIL HIDDEN) Interaction with GuestsI live in the main house/studio and will be available as recording/sound engineer, host and any other help I can offer. The Neighborhood146 acres of State forest and VAST trails @ your doorstep. 1 mile to the charming village of Grafton, featuring fine dining @ The Grafton Inn, a great bar & Live music @ Phelps Barn, Skiing, tubing, hiking, swimming @ Grafton Ponds, The Grafton Cheese factory, the Nature Museum and close to golf & skiing @ nearby Okemo and Stratton Mt. Resorts, Tater Hill golf course as well as, Bellows Falls golf course. Getting AroundThere is plenty of parking but access is by a dirt road. during winter and mud season, all wheel drive or a 4x4 is recommended. Other Things to NoteYou need not be a musician/artist to enjoy the serene beauty and quiet. By yourself or as a couple, it's a great escape! For 3 people it would be a cozy experience.
          hotel
          4br hotel
          • Breakfast
          • Gym
          • Parking
          • Pets Allowed
          • Swimming Pool
          • Wifi
          Situated in Chester, this bed & breakfast is 0.7 mi (1.1 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).
          Inn
          6br Inn
            This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe.
            Tower
            1br Tower
              The Tower Room in Hugging Bear Inn and Shoppe, a bed 'n breakfast Inn. Cozy and romantic with queen-sized bed, full private bathroom with shower and air-conditioning for hot weather days. A round room (actually hexagonal) in the tower of this Victorian home overlooks the village green. Full Vermont breakfast made to order every morning. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our other listing for renting the entire Hugging Bear Inn. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe.
              Bedroom
              Bedroom
                Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. Also features a infrared fireplace heater. Full Vermont breakfast made to order every morning. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our other listing for renting the entire Hugging Bear Inn. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition.It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe.
                Bedroom
                Bedroom
                  A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our other listing for renting the entire Hugging Bear Inn. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the Vermont tradition. It is located in the center of Chester, VT, on the green, a very beautiful quintessential Vermont town setting. Stay in one of six guest rooms blending 19th century charm and modern touches, each with a private bath and air conditioning. Rooms accommodate couples, singles, families and children. And you will find a Teddy Bear in every bed! Relax on a spacious wrap-around porch, in the living room, or the cozy den. There is wireless internet access at the Inn and cable television in the common area of the living room. Included in your room rate is a hearty Vermont country breakfast and there is plenty of Vermont maple syrup for your pancakes. Seconds? Certainly! Tea, coffee and fresh fruit is always available in the dining room. Located on the property, the Hugging Bear Shoppe features a wonderful shop with the finest selection of Teddy Bears in the Northeast. You're likely to find anything from aardvarks to zebras and a lot in between. We have the largest selection of Steiff collectibles, artist bears and Muffy Vanderbear in the Northeast. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and endless other bearaphernalia. We welcome children of all ages to this lovely Victorian Inn filled with laughter and Teddy Bears. This place is enchanting and magical. You'll make friends for life here! Inn History: In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester village buildings. The projecting loft gable and the pyramidal-capped cupola distinguish the finely executed barn. In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont. Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase. In 2005, The Hugging Bear Inn and Shoppe ventured into the online world with the launch of its online store. Now, everyone from all over the world can enjoy the Teddy Bears and their friends by purchasing directly over the Internet. Despite the changing times and seasons, you always get friends for life at The Hugging Bear Inn & Shoppe.
                  Farmhouse
                  5br Farmhouse
                  • Pets Allowed
                  Charming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of parking besides). This house was built between 1800 and 1805, it is NOT modernized (we like it this way!), but is very cozy and well-equipped. The two living rooms each have very well-built fireplaces; wood is included. We supply all sheets, towels, and everything you'll need in the kitchen. We have flat screen TV, cable, wireless, and a great old-fashioned game table. (We also have a collection of games that are pre-plastic. :) The house is available now. We rent all times of year. We have a two-night minimum but much prefer to rent by the week or month. A security deposit and cleaning fee are required. Vermont tax is 9%. We do permit pets but there is an additional cleaning fee, and no more than two pets at a time are permitted. Beds: 1 King Bed, 1 Queen Bed, 6 Twin Beds
                  Home/Apartment
                  3br Home/Apartment
                  • Wifi
                  • Parking
                  The SpaceThis timber frame apartment is on the second floor, with hillside views of swaying white pines, stonewalls, blueberry bushes and a clean flowing stream. Skylights and newer timber frame construction add to a bright private space and relaxing atmosphere. Guest AccessUpstairs apartment with plenty of parking, full kitchen and one full bath, two bedroom, loft space, open living and dining area. Interaction with GuestsWe live next door, work on the first floor and are available to help with any questions that might come up during your stay while also respecting your privacy. The NeighborhoodChester is an historical 250 year old town in Vermont with a center Green, recreational areas, bookstore, restaurants, grocery store, shops and registered historical landmark stone houses. Getting AroundThere is not much public transportation but plenty of scenic country roads so bring a car, bicycle or motorcycle to get around. Other Things to NoteWe are located in a relatively rural location, two miles from town with a small glass blowing business located downstairs and in the adjacent building.