Sheffield, MA, United States Accommodations

Accommodations in Sheffield

Home/Apartment
3br Home/Apartment
  • Wifi
  • Breakfast
  • Parking
  • Swimming Pool
Three rooms available- Each with private baths. Rooms starting at $125.00 for The Mews per night, the Pottery Barn Room at $150.00 per night and the Nantucket Suite at $200.00.
Bedroom
Bedroom
  • Wifi
  • Breakfast
  • Parking
  • Swimming Pool
The SpaceLocated on the second floor front corner room of Buttonwood. It has a full size bed with sitting area, private bath and shower. Wonderful view of back pool area, acrage, frog pond, grape arbor, also view of Buttonwood front lawn. We are 2 1/2 hours from Boston and 2 hours from NYC. (Wassaic NY commuter rail to Grand Central Station is 25 minutes drive) The property has many things available for your comfort and enjoyment. In Summer an inground heated pool with cabana, grape arbor with frog pond, spacious yard with soccer goals, vollyballor badmitten, tree swing and several outdoor seating areas. Enjoy sunsets in the adirondack chairs by the firepit or dine on spacious screen porch or stone patio. Cook on the Vicking range or grill on the Vermont Castings outdoor grill. Winter offers cosy fires in the 60" colonial fireplace, a large HD TV with DVD's in the family room. views of mountains in three states from the large colonial windows. The property is 15 minutes from Great Barrington with its great shopping, restaurents and the Mahawie Theather. 20 minutes from Norfolk, Ct and Infinity Music Hall and restaurant. Stockbridge is 25 minutes north on Rt 7 with fun shops, the Red Lion Inn, Norman Rockwell Museum, Daniel Chester French Museum and Tanglrwood just down the road. The Ashley Falls area is well known for its great biking both touring and casual. The Housatonic river boat landing is 1/4 mile from the property for canoeing and kyaking, Winter skiing is 13 miles to Butternut, 14 miles to Catamount. The Salisbury School is 7 miles, The Hotchkiss School is 12 miles, The Berkshire School is 7 miles, Lime Rock Park is 11 miles. Many antique shops are in the Sheffield area 3 miles north on Rt 7, Twin Lakes, Ct. for boating and fishing is 6 miles.
Bedroom
Bedroom
  • Wifi
  • Breakfast
  • Parking
  • Swimming Pool
The SpaceVery nice room with two windows overlooking Berkshire Mts. Queen size antique bed, sitting area, desk, bureau with large mirror and drawers, full private bath. Also has seperate private sitting area with Futon that will sleep two with access to private bath. Total access to wireless internet. "Buttonwood" a revolutionary war era Georgian/Federal country home is named after the large centuries old Sycamore tree in its front yard; one of the largest in Massachusetts. This bucolic setting, surrounded by 60 acres of corn fields is 2 1/2 hours from Boston and 2 hours from New York City (Wassaic commuter rail to Grand Central Station 25 minutes drive) Buttonwood has many things available for comfort and enjoyment. In summer an inground heated pool with cabana, grape arbor with frog pond, cottage with flat screen sleeps 5, spacious yard with soccer goals. vollyball or badmitten, tree swing and several outdoor seating areas. Enjoy sunsets in the adirondack chairs by the firepit and dinner on the spacious screen porch or stone patio, Cook on our Viking range or grill on the Vermont Castings grill. Winter offers cosy nights by the 60" colonial fireplace with several flatscreen TV's numerous DVD's, games, an extensive library and views of mountains in three states from the large colonoal windows. Buttonwood is 15 minutes from Great Barrington with its great shopping, restaurants and the Mahawie Theater. We are 20 minutes from Norfolk, Ct. and the great Infinity Music Hall and restaurant. Stockbridge is 25 minutes north on Rt 7 with its fun shops & restaurants, Red Lion Inn, Norman Rockwell Museum, Daniel Chester French Museum and Tanglewood just down the road. The Ashley Falls area is a great area for biking both touring and casual. The Housatonic river boat landing is 1/4 mile from the property for conoeing and kyaking, Skiing is 13 miles to Butternut and 14 miles to Catamount, The Salisbury School is 7 miles, the Hotchkiss School is 12 miles, The Berkshire School is 7 miles. Lime Rock Park is 11 miles. Many antique shops are in the Sheffield area 3 miles, Twin Lakes, Ct. for boating and fishing is 6 miles.
Bedroom
Excellent
16 reviews
Bedroom
  • Wifi
  • Breakfast
  • Parking
  • Swimming Pool
The SpaceQuaint bedroom with two single beds, private bath with great shower, is on ground floor, next to large family room with large sitting area and main fireplace of the home. Its a really special place . "Buttonwood" a revolutionary war era Georgian/Federal country home located in the village of Ashley Falls, Ma. is named after the large centuries old Sycamore tree in its front yard; one of the largest in Massachusetts. This bucolic setting, surrounded by 60 acres of corn fields is 2 1/2 hours from Boston and 2 hours from NYC. Buttonwood has many things available for your comfort and enjoyment. In summer an inground pool with cabana, grape arbor with frog pond, spacious yard with soccer goals. vollyball or badmitten, tree swing and several outdoor seating areas. Enjoy sunsets in the adirondack chairs by the firepitands dinner on the spacious screen porch or stone patio, Cook on our Vicking range or grill out on our Vermont Castings grill. Winter offers cosy nights by the 60" colonial fireplace with several flat screen TV's numerous DVD's, games, an extensive library and views of mountains in three states from the large colonial windows. Buttonwood is 15 minutes from Great Barrington with its great shopping, restaurants and the Mahawie Theater. 20 minutes from Norfolk, Ct and the Infinity Music Hall and restaurant. Stockbridge is 25 minutes north on Rt 7 with its fun shops and restaurants the Red Lion Inn, Norman Rockwell Museum, Daniel Chester French Museum and Tangelwood just down the road in Lenox. The Ashley Falls area ia a great area for biking both touring and casual. The Housatonic river has a boat landing area 1/4 mile from the property for conoeing and kyaking, Skiing is 13 miles to Butternut and 14 miles to Catamount, The Salisbury school is 7 miles, the Hotchkiss School is 12 miles, The Berkshire School is 7 miles. Lime Rock Park is 11 miles. Many antique shops are in the Sheffield area 3 Miles, Twin Lakes, Ct for boating and fishing is 6 miles
Home/Apartment
1br Home/Apartment
  • Wifi
  • Parking
The SpaceWe are in a rural area. Our home is on a quiet, residential road and we reside in the main house. The apartment comfortably accommodates one or two people. There are many attractions to take advantage of especially if you like the outdoors, great restaurants and quaint New England towns like Great Barrington, Stockbridge and Lenox. There is a wide array of dining opportunities, charming general stores, antiquing and boutique shopping within minutes. There are also numerous hikes available within a few miles listed with the Trustees of Reservations. Sections of the Appalachian Trail are also nearby. We are available to help you discover the area. Guest AccessParking, wifi, . Interaction with GuestsWe are generally available to answer questions and provide assistance. The NeighborhoodCalm, quiet and beautiful. Getting AroundThere is no real public transportation. You will need a car. Other Things to NoteBecause of space limitations, we do not allow additional guests to stay with you in the apartment. Sorry no pets.
Bedroom
3br Bedroom
  • Wifi
  • Parking
The SpaceMy house has an eclectic decor gathered from around the world. It is a cozy and comfortable home a short distance to either Butternut or Catamount Ski Slopes as well as to Great Barrington where there are many shops and restaurants to satisfy everyone's appetites and curiosity. Theater, music and art are in abundance in the Berkshires as well as hiking and other outdoor activities. My kitchen is fully equipped for preparing your own meals with a dining table that easily seats 10. I do have a cat who will be fed by someone who rents my studio in the garage - (also uses the downstairs bath on occasion). The cat is not allowed upstairs so it is clean of any cat dander and has its own cat door to go in-out on its own. Guest AccessAlthough I do not usually lock my doors (there is absolutely no crime here in Ashley Falls/Sheffield, MA) I will be happy to leave you with a key so that you can lock the door if you feel more comfortable doing so. There is a large backyard for you to use as you please (a bonfire, perhaps? or building snowmen!) depending on the weather. Interaction with GuestsInteraction with guests is contingent on their needs for usual AirBnB stays when I am home; one to four weeks per year, and in this case 3 weeks, I will be away when the whole house will be yours. I will be happy to leave you with any information about "things" going on in the area and hopefully we will have extended talks to answer any and all questions you may have before you arrive; I will also leave my cell number so you can reach me by phone, should the need arise. The NeighborhoodDowntown Ashley Falls is actually a hamlet of Sheffield, MA, consisting of a Post Office. Sheffield and northern CT are known for their antique stores/auction (once a month). Great Barrington (the next town north on Rt 7) is a bustling small town with many fine restaurants (Japanese, Thai, Indian, Chinese, American/French/Italian) serving mostly local and/or organic food and great stores. Spreading out from here and close by is Tanglewood, Shakespeare & Co, Edith Wharton's Home - The Mount, as well as many more music, dance, theatre venues and museums and galleries; in the winter two ski resorts are equidistant for your enjoyment. Rivers and Falls abound for hikes and swimming. Getting AroundYou most certainly will need a car as this area has the poorest of poor public transportation. A car is therefore a given; parking on the property is no problem (the garage holds one car but there is plenty of room outside for others. The nearest airport is Bradley in Hartford, CT or the Albany, NY airport where you can rent cars if you are flying in from somewhere far. GPS works as well as my preference, real paper maps from AAA or elsewhere. And of course, I can give you instructions more detailed to getting to my home and/or somewhere else nearby. Other Things to NoteI have arranged for snow-plowing if it becomes necessary (more than 4/5 inches). The garage only parks one car so there is no need to shovel it out; only the two front steps will need to be shoveled if it snows. I have the house cleaned once a week through Elder Services who require that someone be here the whole time they are here (2-2 1/2 hrs on Monday afternnoons). For an extra charge, in the event you cannot be here during that time, I can get someone else to come and clean at your convenience. You will, of course, have to let me know ASAP so that I can make arrangements.
Home/Apartment
3br Home/Apartment
  • Wifi
  • Parking
The SpaceThis property is in the highly sought after Bershire Vacation area for your year round summer, fall foliage and winter wonderland vacations. A very short drive to skiing at Butternut & Catamount. If you like shopping you are just minutes from Lee Outlet Mall. Historic Stockbrige is nearby. Summer rentals feature Tanglewood, Shakespeare Festival, hiking and kayaking. Great biking! Close to Lime Rock racing. Guest AccessGuests will have access to entire house. Interaction with GuestsOwner will correspond with renters and work out any interactive arrangements. The NeighborhoodBeautiful views and located near route 7 and all local attractions Getting AroundThere is no public transportation to speak of Other Things to NoteFinely detailed home antiques, good linens, top quality beds ect..
Home/Apartment
Excellent
8 reviews
3br Home/Apartment
  • Wifi
  • Parking
The SpacePerfect, cozy, Berkshire getaway in close proximity to outdoor and arts attractions in the area. The ranch style house is in a quiet neighborhood in Sheffield, MA with 3 bedrooms, 1.5 bath, dining room, screened in porch, large living room, and great sized kitchen. Can sleep 6 people in bedrooms and up to 2 on the pull out couch in the living room. A wonderful place to come if you're visiting the area to ski, cycle, go to Tanglewood, hike, and/or enjoy great quality local food and fine dining. 2.5 hours from NYC and Boston. Local attractions: Great Barrington (shops, grocery store, etc) - 10 minutes Butternut - 20 Minutes Catacmount - 20 minutes Appalachian Trail - 10 minutes Tanglewood - 25 minutes Guest AccessGuests will have full access to the house and are welcomed to use the washer/dryer and any cooking supplies and appliances. A letter with more details about your stay will be sent to you once the reservation is confirmed. Interaction with GuestsI am currently living full time in NYC so when the house is fully rented, guests will have the place to themselves. I will be available via phone, email, text or AIRBNB messenger before or during your stay if you have any questions.
Home/Apartment
5br Home/Apartment
  • Wifi
  • Parking
The SpaceEnjoy the elegance of this charming colonial at an equally attractive rate. It is modestly furnished with all of the essentials for a lovely, relaxing stay. There are four bedrooms - three with full to queen sized beds and one with twin trundles. In addition, the large loft has two full sized beds. A queen sized inflatable mattress is available upon request for additional sleeping space in the carpeted room below the loft. Guest AccessGuests have full access to the house except for the garage, basement, and attic. There is also a beautiful 1,600 square foot open studio on the property which can be rented for parties, retreats, reunions, conferences, and more at an additional rate. Contact us for details. There is wifi, but no TV. The fireplace is not usable. Interaction with GuestsSchedules permitting, we will arrange to meet you upon check in and check out. If not, we will leave a key for you. We are available to answer questions, offer suggestions for things to do, places to eat, etc., but will let you dictate how much interaction you'd like from us. Someone may be on the property (in the studio, but not in the house) during the course of your stay The NeighborhoodSheffield offers some fantastic outings including tours of the Magic Fluke ukulele shop, Big Elm Brewery, and Berkshire Mountain Distillery. There is fantastic hiking in the area ranging from a variety of trails at Bartholomew's Cobble to the miles of Appalachian Trail including the rigorous Race Mountain. The valley offers fantastic bike riding with panoramic views. The Market Place Cafe, just a five minute walk, and Stage Coach Tavern are some great dining options. Getting AroundThere is plenty of parking. Rides from Bradley and Albany airports as well as the Wassaic and Hudson train stations can be arranged for an additional fee. Other Things to NoteOur 1,600 square foot studio building is an ideal space for functions, workshops, retreats, and more. Formerly a state of the art recording studio, the space can still serve as one for bands and artists looking to get away to record, as well as a beautiful space for a yoga, fitness, or meditation retreat, film screenings, family reunions, small ceremonies, and more.
Home/Apartment
3br Home/Apartment
  • Wifi
  • Parking
The SpaceThis lovely home features an open living space with a full, spacious gourmet kitchen with recently updated appliances. The home has three spacious bedrooms, with two full bathrooms. The master bedroom suite has a connected private bathroom with a walk-in shower and jacuzzi tub. In the warmer months guests can relax on the porch overlooking the wooded backyard. Towels and linens are provided for guests. Guest AccessGuests have access to the whole home. The NeighborhoodSheffield is a quintessential New England town. The home is located only minutes from town on a quiet country road where you can easily escape your busy life to slow down and relax. Getting AroundA car is necessary for this area. Other Things to NoteLocal Attractions: Sheffield - (town center) 5 minutes Great Barrington - 10 minutes Butternut Ski Area - 20 minutes Catamount Ski Area - 20 minutes Tanglewood (Lenox) - 30 minutes
Home/Apartment
2br Home/Apartment
  • Wifi
  • Pets Allowed
  • Parking
The SpaceA real rustic space in the country. The perfect antidote to civilization. Guest AccessClose to all Berkshire attractions--20 minutes to Tanglewood and Jacob's Pillow, 15 minutes to skiing or swimming, 10 minutes to downtown Great Barrington and a number of Organic Farms. Only 2.5 hours from NY or Boston. Interaction with GuestsThere is a caretaker on property in the converted barn loft who can answer questions and handle simple requests. Getting AroundYou need a car. Other Things to NoteSee our house featured in the New York Times Great Homes and Destinations section! (URL HIDDEN)
Home/Apartment
3br Home/Apartment
  • Wifi
  • Pets Allowed
  • Parking
This property was deactivated by the owner. We have found several other available options for your stay.
Home/Apartment
2br Home/Apartment
  • Wifi
  • Pets Allowed
  • Parking
The SpaceThis perfect Berkshire retreat on beautifully landscaped grounds is the ultimate escape. Vacation in style in this tastefully renovated cottage. Entertain in the open gourmet kitchen or spread out onto the back deck for grilling or relaxing in the redwood hot tub. Hangout and spend the day enjoying the private grounds and beautiful perennial plantings. The picturesque roads of Sheffield offer some of the best biking in New England. A stones throw from the Appalachian Trail among many other ideal hiking spots. When it comes to culture and entertainment the Berkshires has such a wide array of activities for any and all. Located equidistant between the two local ski areas Catamount and Butternut this makes a great winter getaway.
farmhouse barn
Excellent
4 reviews
3br farmhouse barn
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and botanical gardens.
    Home/Apartment
    4br Home/Apartment
    • Wifi
    • Pets Allowed
    • Parking
    • Swimming Pool
    The Space3600 sq. ft. Renovated Horse Barn Guest AccessThe entire house Interaction with GuestsYes I am just a phone call away & I have staff to assist. The NeighborhoodBeautiful rolling hills & meadows, farm country, Housatonic River, 1/3 mile to Appalachian Trail. Getting AroundYou need a car, rentals available nearby. Other Things to NoteThere is a complete brochure about the house upon arrival.
    Home/Apartment
    2br Home/Apartment
    • Wifi
    • Breakfast
    • Parking
    The SpaceThis recently renovated single level 1,250 square foot open plan renovation provides a great room that is spacious, comfortable and relaxing with a queen size convertibles couch and two antique club chairs, an adjustable wing chair, vintage side and coffee tables and a flat screen TV connected to Time Warner Cable and Wi-Fi. The rest of the open space is filled with a dining area with period Art Deco table & chairs under a complementary chandelier. Across from this is the fully functional white kitchen, spiced with red accents including a vintage Coca-Cola panel from a Spanish language dispensing machine. Down the carpeted hallway are two bedrooms, each fitted with a queen size bed, antique dressers and night tables. A separate WC is directly across the hall and next to the WC is a luxurious shower / dressing room furnished with an all-glass round shower, an antique dressing table and chair with appropriate lighting and an antique Kimono stand to hang wet towels. Next to the front door is a desk with local maps, brochures and emergency telephone numbers and a cork board for you to leave messages for members of your group. Guest AccessGuests will enjoy the convenience and privacy of the bungalow with a fully equipped kitchen, a private screened in gazebo right outside the back doors with a dining set and lighting for after dark. Interaction with GuestsInteraction with guests, after providing the house keys and giving them a basic tour of the interior, will be strictly up to the guests. We live in the house right across the driveway and are available to accommodate any reasonable request that will make their stay more pleasant. The NeighborhoodSheffield is a beautiful example of the best of small-town New England and it is located in Southern Berkshire County, MA. Conveniently located about 1 1/2 hours from the international airports at Hartford and Albany. The drive from NYC or Boston is about 2 1/2 hours (in reasonable traffic). The Bungalow is at 125 South Main Street (Rte. 7) within walking distance of Sheffield's town center. The Berkshires are adjacent to the Mid Hudson Valley, N.Y. and the Litchfield Hills of Connecticut with their scenic and historical attractions, shopping and restaurants from fabulous to fast food. AUTUMN IS HERE! The days are bright, cool and clear the temperatures are about 50degrees in the daytime and the nights are in the mid to low 30's. The leaves have turned and we had a full day of snow. We are a short drive (about 16 minutes) to either Ski Butternut or Catamount Ski areas and both offer summer out activities. Our neighbor Immediately south of us just across the lawn, is a country store /Café "The Blue Door". They stock basics for meal preparation, wine and beer and they serve breakfast. Up the road is "The Bridge Restaurant", it is adjacent to the reconstructed covered bridge and a canoe / kayak launch site on the Housatonic river. We are a 12 minute drive to Great Barrington with its restaurants, shopping &The Mahaiwe Performing Arts Center, Fairview Hospital and the revived Fair Grounds. Up scale restaurants line Railroad Street, at the top is Martin's for breakfast all day, great pancakes (David loves the "Tower Bagel"). Approximately 20 minutes further up Rt. 7 you will come to Stockbridge, famous for the Red Lion Inn, the Norman Rockwell Museum and Chesterwood. Nearby is the town of Lee at Exit 2 of the Mass Pike ( I-90 ), a lovely village full of fun shops, very good restaurants, try the crepes at "The Starving Artist Café", and The Lee Outlets. Lenox hosts; Shakespeare & Co, The Mount, Tanglewood, Ventfort Hall Museum, Arrowhead (the former home of Herman Melville with the view that was the inspiration for “Moby Dick”), The Frelinghuysen Morris House & Studio and many shops and a variety of restaurants. For outdoor activities Sheffield offers the Appalachian Trail, Bash Bish Falls State Park, Mt Everett, Mt Washington, and the Housatonic River for fishing and kayak and canoe trips and bicyclists love the local scenic roads. Other southern Berkshire towns offer many ponds, Lake Mansfield, Lake Garfield and York Lake State park. Fall is the turkey, deer and black Bear hunting season as well as upland game bird season you can buy your appropriate licences at Town Hall! A short trip, about 6 miles south on Rt. 41 south, and you are in Connecticut for boating and fishing at Twin Lakes. Several preparatory schools are nearby; The Salisbury School is 7 miles, The Berkshire School is 7 1/2 miles, The Hotchkiss School is 12 miles. For you gearheads Lime Rock Park is 11 miles south in Connecticut. Sheffield has several antiques shops including Susan Silver for fine quality English and Asian antiques, Painted Porch is across the road for country French and English items, Dovetail is just a bit north for clocks and the Emporium, Great Finds and The Great Barrington Antique Center are some of the group shops in Great Barrington. Nearly all of the surrounding towns and villages have at least two antique shops. Getting AroundA car is necessary, we have parking space for up to three visitor's cars on the property. Directions from the Albany Airport or Bradley Airport (Hartford Ct.) are available on their online web sites and on (SENSITIVE CONTENTS HIDDEN) maps . Driving time from either airport is approximately 1 1/2 hours. PLEASE NOTE; BRING YOUR CELL PHONES. We have very good service from most major carriers. Other Things to NoteMinimum stay is two nights usually Friday and Saturday although we welcome midweek guests as well. We are flexible as to check in. Check out on Sunday is before 11:00AM. If we have guests scheduled for Monday we can hold your luggage until 8:00PM if you like.
    Home/Apartment
    Excellent
    5 reviews
    5br Home/Apartment
    • Wifi
    • Parking
    The SpaceOur home is a sparkling mountain style house with two master bedrooms, two kitchens, two large living rooms, a farmhouse kitchen table that seats 20, immense wrap-around deck with bbq and dining table, screened porch and endless views of the Berkshire mountains. Guest AccessGuests have access to the whole house with use of canoe
    Home/Apartment
    3br Home/Apartment
    • Wifi
    • Parking
    The SpacePrivate wooded lot with mature landscaping. Outside patio with hot tub. Interior has master bedroom downstairs with bath. Upstairs has bedroom with double bed and back bedroom has 2 twin beds. Upstairs also has office room and full bath. Laundry in basement. Main floor has large kitchen with farm table seating for 8. Living room has flat screen t.v. and gas fireplace. Guest AccessAccess to whole house and attached garage Interaction with GuestsHost or assistant will be available upon arrival. The NeighborhoodQuiet private neighborhood. Getting Aroundtaxi and bus.
    Home/Apartment
    2br Home/Apartment
    • Wifi
    • Parking
    The SpaceA labor of love, my wife and I transformed a dirt floor garage into a country elegant carriage house with lots of glass, French Doors, and skylights. The light in the second floor great room is spectacular. The main floor consists of a huge master bedroom with a sitting room and en suite bath and a second bedroom with a full bath and laundry right outside the door. All three baths are tile with large showers and antique vanities and soapstone tops. The modern kitchen has stainless steel appliances, soapstone counters and a large island. There is a brick patio with gas grill. The location is walking distance to the center of Sheffield 10 minutes to Great Barrington MA., 20 minutes to Stockbridge MA., short drive to swimming and skiing. Guest AccessYou will be met by our agent who will provide a key and answer any questions you may have. Weekly cleaning is included in the price for short term rentals. I am available by phone or email for any questions that may arise. Interaction with GuestsWe have a local property manager available for emergencies. The NeighborhoodWe also own a restored 18th century colonial located on the same property at a comfortable distance. It houses an apartment with the same couple as tenants for 10 years and a small private office with 9 year tenants. They generate no noise or distraction and our large parking lot provides tons of parking space.
    Bedroom
    Bedroom
    • Wifi
    • Parking
    The SpaceThe Juliet Suite looks out over the orchard and pasture on Wolfe Spring Farm, a working organic farm in bucolic Sheffield. A great location to get to Tanglewood, Sharon Playhouse, the appalachian trail, Bartholomew's Cobble, Shakespeare and Company, Great Barrington and Mahaiwe Theatre OR stay on the farm and hike, bike, fish, canoe or pick fruit. Guest AccessYou have access to a comfortable living room, a huge deck, a chef's kitchen a dining room with a farmhouse table and a large vestibule where you can store your bike, cross-country skis or gear. This room also has laundry facilities. Interaction with GuestsWe live on the farm (out of sight behind the barns) and we have the skills to help with any little difficulties. Our family has lived in the area for over 200 years and we know it well. The NeighborhoodThere are six farms on one side of our four mile road, all connecting in the back to provide great walks and access to the river. On the other side of the road are mountain trails and views. We are close to all the Berkshire attractions but we are also a place where you can be completely Alone. Getting AroundPark on site right in front of the cottage. A car is recommended. We are 40 minutes from Wasaic train station and 1 hour from Bradley airport in Hartford Other Things to NoteThe house has all of the historic charm expected from an 1840 cottage and all of the comfort and function of a "torn to the studs" renovation. It has been soundproofed, climate controlled and built for comfort.
    Bedroom
    Excellent
    9 reviews
    Bedroom
    • Wifi
    • Parking
    The SpaceThe Empire Suite looks out over the mountains surrounding Wolfe Spring Farm, a working organic farm in bucolic Sheffield. A great location to get to Tanglewood, Sharon Playhouse, the appalachian trail, Bartholomew's Cobble, Shakespeare and Company, Great Barrington and Mahaiwe Theatre OR stay on the farm and hike, bike, fish, canoe or pick fruit. Guest AccessYou have access to a comfortable living room, a huge deck, a chef's kitchen a dining room with a farmhouse table and a large vestibule where you can store your bike, cross-country skis or gear. This room also has laundry facilities. A short hike brings you to the sunset overlook with a lean-to and comfortable chairs. Interaction with GuestsWe live on the farm (out of sight behind the barns) and we have the skills to help with any little difficulties. Our family has lived in the area for over 200 years and we know it well. The NeighborhoodThe Neighborhood There are six farms on one side of our four mile road, all connecting in the back to provide great walks and access to the river. On the other side of the road are mountain trails and views. We are close to all the Berkshire attractions but we are also a place where you can be completely Alone. Getting AroundGetting Around Park on site right in front of the cottage. A car is recommended. We are 40 minutes from Wasaic train station and 1 hour from Bradley airport in Hartford Other Things to NoteThe house has all of the historic charm expected from an 1840 cottage and all of the comfort and function of a "torn to the studs" renovation. It has been soundproofed, climate controlled and built for comfort.
    Bedroom
    Excellent
    12 reviews
    Bedroom
    • Wifi
    • Parking
    The SpaceThe Baldwin Suite is one of three suites in Apple Cottage and one of four suites on the farm. The Baldwin is a first floor suite with a brand new double pillow top bed. It has an ensuite bath with shower and a coffee bar. Guest AccessYou have access to a comfortable living room with smart TV, a huge deck, a chef's kitchen a dining room with a farmhouse table and a large vestibule where you can store your bike, cross-country skis or gear. This room also has laundry facilities. Interaction with GuestsWe live on the farm (out of sight behind the barns) and we have the skills to help with any little difficulties. Our family has lived in the area for over 200 years and we know it well. The NeighborhoodThe Neighborhood There are six farms on one side of our four mile road, all connecting in the back to provide great walks and access to the river. On the other side of the road are mountain trails and views. We are close to all the Berkshire attractions but we are also a place where you can be completely Alone. Getting AroundPark on site right in front of the cottage. A car is recommended. We are 40 minutes from Wasaic train station and 1 hour from Bradley airport in Hartford Other Things to NoteThe house has all of the historic charm expected from an 1840 cottage and all of the comfort and function of a "torn to the studs" renovation. It has been soundproofed, climate controlled and built for comfort.
    Home/Apartment
    3br Home/Apartment
      The SpaceWe provide charm, comfort and cleanliness and we provide for every little need. The pantry is stocked with staples and you will find our farm fresh eggs in the fridge. Guest AccessThe entire house welcomes you including a very large deck, a dining room that seats 12, a mudroom with plenty of storage for bikes, skis or even a kayak (and a laundry room), a chef's kitchen with a walk-through pantry and a very comfy living room with a fireplace and smart TV. Interaction with GuestsWe live in another house on the farm (behind the barns). We are nearby and happy to help if you have questions or if you want a farm tour! The NeighborhoodSheffield is famous for its open space and outdoor experiences. We are 10 minutes away from Great Barrington (Smithsonians Best Small Town USA 2012) and twenty minutes from the Norman Rockwell Museum, Tanglewood, the Berkshire Theatre Festival and Shakespeare and Company. Getting AroundA local bus comes to Sheffield. If you are planning to canoe or kayak, ask us about river pick-ups Other Things to NoteThere are 54 acres of woods and fields and mountain views accessible for hiking, cross-country skiing or mountain biking. Just next to the parking area is a trail that goes to the sunset lean-to. We are close to other natural wonders as well as the Berkshire Theatre Festival, Sharon Playhouse, Tanglewood , Shakespeare and Company, the Mahaiwe, Berkshire Choral Festival, Golf courses and much more
      Home/Apartment
      Excellent
      13 reviews
      3br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      The SpaceA three bedroom house with indoor hot tub, den and large living and dining area. One bedroom has a queen, the other a full and the other a twin. There is bathroom upstairs with tub and the bathroom downstairs has a stall shower. The den has a futon. There is cable TV and wifi and a sound system throughout the house. There is a screened in porch and a porch that overlooks the pond and the woods and eastern ski. Interaction with GuestsWe will not be there during your stay The NeighborhoodWe are located in the Southern Berkshires 15 minutes from Butternut and Catamount ski areas, wonderful restaurants in Great Barrington, amazing hiking and cultural events.
      Chalet
      3br Chalet
      • Wifi
      • Parking
      Guest AccessThere is an abandoned barn on the property. Guests are not allowed to access this barn. Interaction with GuestsWhen the house is rented, we typically stay with family about ten minutes away. So if there is ever an emergency, we can help. We will be easily reachable by phone, text, and email. Getting Around20 minutes to the charming town of Great Barrington, with great restaurants, shopping etc. 40 minutes from Metro North to New York City. There are taxi services from the train station.
      Home/Apartment
      3br Home/Apartment
      • Wifi
      • Parking
      The SpaceMy home comfortably sleeps 6. Large windows facing south bring the shared living space feel bright and open. Perfect for a family getaway! Guest AccessGuests will have access the entire property Interaction with GuestsI am available as needed and able to answer any questions or requests promptly. I also live nearby The NeighborhoodQuiet neighborhood. Local attractions include skiing, boating, hiking, shopping, yoga, entertainment close by Getting AroundYour own vehicle is needed. Other Things to NoteSmart tv with wifi, no cable. No public transportation
      Bedroom
      Bedroom
      • Wifi
      • Parking
      The SpaceMy local realtor called my guest suite....funky:) It's actually the first floor of an 1810 New England farm house. The original staircase from the main kitchen leads to the master bedroom, den and newish bathroom. A separate dbl. bedroom is also available. So for an extra fee, I can accommodate 2 couples if they are willing to share the bathroom. Please contact me if you wish to explore this option. I've traveled all over the world and this is where I have chosen to make my permanent home:) Interaction with GuestsI love this area and would be very happy and interested to help you plan your trip. The NeighborhoodUnique in the world. The Berkshires are called America's #1 Cultural Resort. 25 minutes to Tanglewood. 20 minutes to Berkshire Theatre Festival, 40 minutes to Barrington Stage and the Colonial Theatre, Pittsfield. 50 minutes to the Williamstown theatres, The Clark, and Mass Moca.....etc:) Getting AroundYou really have to have a car to get the most from your visit...:)
      Bedroom
      Bedroom
      • Wifi
      • Breakfast
      • Parking
      The SpaceThe room, the bathroom, the living room and the private deck all look out on a stunning vista of mountains and pastures, sometimes with horses grazing. Enjoy the tranquility, the privacy and the knowledge that every watt of energy you use is provided by the sun. The plentiful hot water is also heated by the sun. It's a pleasure to walk around the farm or to the surrounding areas, like the river. You can enjoy home grown strawberries, raspberries or apples. You might even collect eggs or milk a cow! Guest AccessA big comfortable living room with a stone fireplace and smart TV, a dining room with a farmhouse table that seats 10, a fully stocked kitchen with farm fresh eggs and berries in season and a beautiful farm to walk, hike, bike or cross country ski Interaction with GuestsWe greet our guests and stay available for questions by text. We live on the farm. We are rarely indoors but we are always available for questions if you need us. Other Things to NoteThere is an electric car charger available
      Home/Apartment
      Good
      4 reviews
      3br Home/Apartment
      • Breakfast
      • Parking
      The SpaceRed Door 23 has an open floor plan to allow for easy entertaining between the kitchen and the living space. A small wood stove creates ambiance in the winter, and giant sliding glass doors create easy indoor-outdoor living in the summer. The three spacious bedrooms are sunny and clean with simple decor. A large and lush backyard provides space for kids, gardening, and grilling. The Berkshires is the ideal setting to reconnect with nature while still having access to zagat-rated restaurants and lively entertainment. Located equidistant (only 2.5 hours) to New York City and Boston for anyone looking for an extra adventure! Guest AccessEntire house, driveway, and private lake. Interaction with GuestsI am available by cell phone at any time. I would be more than happy to provide recommendations on food/activity for your stay. I live ten minutes away in case of an emergency. The NeighborhoodThe immediate neighborhood is woodsy, but still in sight of your nearest neighbor. Sheffield is filled with farms and has a quaint town center. The local brewery and distillery provide weekend tours to the public. The Berkshires has an endless supply of amazing restaurants and outdoor activities to discover. Additional attractions include: Great Barrington (10 minutes away) -Named "Greatest Small Town" by Smithsonian Magazine -Mahaiwe Theater -Butternut Ski Resort Stockbridge (20 minutes away) -Norman Rockwell Museum -Original Red Lion Inn Lenox (30 minutes away) -Tanglewood (Boston Symphony Orchestra outdoor concerts) -Kripalu Yoga Center- World renowned Other Bosquet Ski Resort Catamount Ski Resort Jiminey Peak Ski Resort Mass MoCA- Museum of Contemporary Art Hiking Trails Antiques Getting AroundA car is recommended anywhere in the Berkshires. Ample driveway space available.
      Cottage
      Excellent
      4 reviews
      3br Cottage
        Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and botanical gardens.
        Home/Apartment
        4br Home/Apartment
          This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the performing arts experience, relax around the outdoor fireplace or enjoy the large winter porch sipping on hot chocolate- you will not be disappointed! With 4 bedrooms and 2 bathrooms, this 4,800 square foot home comfortably accommodates 8 people. With it's rustic yet modern charm and amenities, this home provides the perfect balance of relaxation and convenience that every vacation desires.The many amenities include a sound system through-out the home and the outdoor grounds. The home theatre room with its 62" LED flat screen is complete with an extensive blue ray collection and comfortable leather seating. An American Heritage pool table sits center stage in the game loft that includes many board games, puzzles and collection of gaming consoles. The living room is the perfect spot to cozy up and rest or read a book while sitting in front of the fireplace. The kitchen is well equipped with hi end Viking/ Wolf appliances including a Chefs collection oven along with all the essentials to cook, bake and entertain. Separate formal dining room compliments this home while the in-kitchen bar seating is perfect to grab your morning coffee or you may choose to sit in the sitting area and watch the birds while they enjoy their morning feast. The secluded upstairs master bedroom has a Tempurpedic king size bed with luxurious down bedding. The perfect chair is tucked in to quietly read or enjoy the wooded view from the windows. A 5 jet jacuzzi bathtub is always waiting nearby to enjoy after a day filled with skiing and snowboarding for the ultimate zen relaxation. Downstairs host 3 more bedrooms 2 with bunk beds and another with a queen, all with luxurious down bedding to keep you warm during Berkshire winter nights. Other amenities include a radiant floor heated mudroom perfect for keeping ski boots warm and ready for your next slope adventure along with a laundry room, and an automatic generator as well as a small loft with a desk and wireless internet access and cellular phone service via AT&T microcell.
          Home/Apartment
          5br Home/Apartment
          • Wifi
          • Pets Allowed
          • Breakfast
          • Parking
          The Berkshire 1802 House is close to family-friendly activities including hiking trails, live music and theater, as well as great restaurants. You’ll love my place because of the ambiance in the bedrooms, public spaces including the grounds. The house is good for couples, solo adventurers, and business travelers. We have 5 rooms available for guests. We can accommodate up to 12 guests with double occupancy (the rate per room $110) and 2 rooms have an extra twin bed besides the main bed.
          Bed & Breakfast
          Bed & Breakfast
          • Parking
          • Pets Allowed
          • Wifi
          Staveleigh House Bed and Breakfast is conveniently located on Route 7 in historic Sheffield, Massachusetts. Our comfortable and affordable B&B has 7 rooms all with private baths. We’re just minutes away from many fine restaurants and shopping in Great Barrington and close to major Berkshires venues. The rooms are Queen, King and Twin bedded, all are air conditioned and most have cable TV. WiFi is available throughout the inn. Breakfast features fresh roasted coffee, seasonal fruit and a hearty entree.