Chestertown, MD, United States Accommodations

Accommodations in Chestertown

Home/Apartment
1br Home/Apartment
  • Wifi
  • Parking
The SpaceThe space includes kitchen/living room combo, bedroom with queen size bed. The bathroom has a shower and tub. An outdoor deck with cafe table and chairs is a nice place to lounge on a sunny day. The apartment is furnished with hand-made, reclaimed wood furniture created by Chora Studio. It is also decorated with works by local artists. The apartment is conveniently located in downtown Chestertown. It is close to Washington College and the Chester River waterfront. It is adjacent to the beautiful Memorial Park. A wonderful place to stay for a weekend retreat in an historic, quaint town on the Eastern Shore of Maryland. Perfect for families, couples, artists, writers, musicians and scholars. Available for short or long stays. Comes with one parking space. Ample street parking nearby. There is an adjacent downstairs apartment, which can be combined with this listing. https://www.airbnb.com/rooms/4044138 They can be connected via internal stairs to accommodate a total of 4 guests. Guest AccessPrivate entrance via outdoor stairs. The apartment is located on the 2nd Floor. Interaction with GuestsThe owner occupies the apartment next door. She is available to assist during your stay. The NeighborhoodCharming, quiet, safe neighborhood in a historic, college town. It's a great location to enjoy many of the annual events in the area: National Music Festival Tea Party Festival Washington College Graduation and Events RiverArts Classes & Events Sultana Downrigging Weekend Kent County Poetry Festival Chestertown Taste of the Town Fourth of July in Kent County River-Fest Chestertown Jazz Festival Chestertown Historic Walking Tour Chestertown RiverArts Studio Tour Holiday Winterfest Getting AroundA car is necessary if you need to get anywhere outside of the town. You can walk easily to anywhere in downtown Chestertown and Washington College is within walking distance. Uber is a new option in Chestertown. Other Things to NoteIf you need a place to accommodate 4 people, consider our DUPLEX listing. https://www.airbnb.com/rooms/4044138 We also have 2 cottages 12 miles from Chestertown located by the Chesapeake Bay. Bayview accommodates 4 guests: https://www.airbnb.com/rooms/2557288 Sunview accommodates 5 guests: https://www.airbnb.com/rooms/6324194
Home/Apartment
Excellent
65 reviews
3br Home/Apartment
  • Wifi
  • Parking
The SpaceCombing southern living with the sophistication of London. This is an in town Historic 1880 house that has been expanded and completely renovated. New exterior, kitchens, baths, bedrooms, family room, porches, pergola. Nine foot plus ceilings accented with architectural custom designed molding throughout. Bright southern exposure kitchen with large entertaining cooking area and family room. Granite counter tops in kitchen, hand tiled, Bosch dishwasher, gourmet 6 burner dual fuel Wolf oven and range. Extra large master bedroom with cathedral ceiling – matching cathedral ceiling in master bath. Master bath with custom black and white tile work, twin sinks, marble counter tops/ standard shower/rain shower/body jets/bench and original claw foot tub. Covered porch off of family room w/ipi mahogany deck. Side cedar beamed arbor pergola off of family room with ipi mahogany deck. Detached garage with professionally finished space above – mahogany floors frame the backyard (not included). Brick and stone patio with beautiful perennial garden –to complete this wonderful property. Guest AccessMain House - King bed in master Queen bed in second bed room Single bed in third bedroom Library/office use for coats only Parking on street in front of house Interaction with GuestsUpon arrival. Owner may be on-site to cut grass, put out recycling and trash (Fri,Sun). The NeighborhoodQuiet tree lined street - two churches with in one block - library across street. One block to JR's Pub and the Lemon Leaf Cafe. No problem to leave the doors unlocked when you step out. Getting AroundWalking or bikes - 12 miles to Rock Hall for fresh Maryland Crabs in season. Other Things to NoteTwo night minimum stay required On holiday weekends there will be a three night minimum stay
Home/Apartment
2br Home/Apartment
  • Wifi
  • Parking
The SpaceSpending time downtown without having to drive again until you leave is a plus. Everyone loves staying downtown if you like people. Guests will have access to restaurants, bakery, shopping, Saturday Farmer's Market, Garfield Center for the Arts, Good walking paths. We can be as flexible as our guests ask for. We love being able to step out on the sidewalk and always see someone we know who is walking their dogs, babies, or just a stroll down to the foot of the street to the Chester River. Wilmer Park is right around the corner where you can sit on park benches and watch the activity on the river and read or just enjoy the scenery. Guest AccessGuests will have access to restaurants, bakery, shopping, Saturday Farmer's Market, Garfield Center for the Arts, Good walking paths. Interaction with GuestsWe are very accessible to our guests. We are only a phone call away. We have been known to take our guests sight seeing, to the grocery store, and fish market for fresh crabs, rock fish and more if requested!! The NeighborhoodWe love being able to step out on the sidewalk and always see someone we know who is walking their dogs, babies, or just a stroll down to the foot of the street to the Chester River. Wilmer Park is right around the corner where you can sit on park benches and watch the activity on the river and read or just enjoy the scenery. Getting AroundWe have had guests who have no transportation. We help whenever requested!!! Other Things to NoteA wonderful get away spot for many reasons. We have had guests here for weddings, golfing, reunions, college weekends and just get away time!!
Home/Apartment
1br Home/Apartment
  • Wifi
  • Pets Allowed
  • Parking
The SpaceNestled behind the main house with it's own entry and private garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Complete with a full kitchen, bath and laundry area, the cottage boasts a queen size bed, roll away bed (or aerobed, guests choice) and wireless internet access. Air conditioning, and little propane stove for comfort. We supply linens, and can stock fridge with advance notice and payment. Water focused community with miles of road for running and bike or motorbike riding. We have parking available for boat or skidoo trailers, as well as day kenneling for pets as space permits.
Home/Apartment
1br Home/Apartment
  • Wifi
  • Parking
The SpaceThe space includes kitchen/living room combo, bedroom with king size bed. Full size pull out couch in living room. The bathroom has a shower. The apartment is conveniently located in downtown Chestertown. It is close to Washington College, Byford Cove and the Chester River waterfront. It is adjacent to the beautiful Memorial Park and a short walk to the iconic Chestertown Fountain Park. This apartment is a wonderful place to stay if you are looking for a weekend retreat in a historic, quaint town on the Eastern Shore of Maryland. Great for artists, writers, musicians and scholars who need a place to stay in Chestertown. It is perfect for a short stay and longer stays are available. There is one parking spot on the premise. Ample street parking is nearby. There is an adjacent upstairs apartment which can be combined with this listing for 4 guests. https://www.airbnb.com/rooms/1274782 Guest AccessPrivate entrance via outdoor stairs. The apartment is located on the 1st Floor. There is a small set of stairs that lead up to the entrance. Interaction with GuestsThe owner occupies an apartment next door. She is available to assist during your stay. The NeighborhoodCharming, quiet, safe neighborhood in a historic, Liberal Arts college town. Getting AroundPublic Transportation is basically non-existent. A car is necessary to get around the town, but you can walk to most places in Chestertown. Uber is a new option in Chestertown. Other Things to NoteThere is an adjacent upstairs apartment which can be combined with this listing. https://www.airbnb.com/rooms/1274782 They connect via internal stairs. If the 2 places are combined it can accommodate up to 4 people. We also have 2 cottages 12 miles from Chestertown located by the Chesapeake Bay. Bayview accommodates 4 guests: https://www.airbnb.com/rooms/2557288 Sunview accommodates 5 guests: https://www.airbnb.com/rooms/6324194
Home/Apartment
3br Home/Apartment
  • Wifi
  • Parking
The SpaceA 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in Chestertown - with views no hotel can match! Chestertown is a quaint historic town on the Maryland Eastern Shore and boasts unique shops, restaurants as well as supermarkets, bowling alley and a cinema. Along with the historic Washington College, the town focuses around the river, where you can take cruises on the Sultana (a 18th Century Schooner), or eat overlooking the river. There are 2 boat ramps in nearby marinas, so bring your boat or jetski for additional fun. The driveway is long enough to park a large vehicle with trailer attached (for example a Suburban with trailer for a 24' boat fits easily). Our house provides 3 bedrooms, an open dining-kitchen area, one main bathroom and a separate lounge that overlooks the river. All rooms are on the same floor. There are 4 kayaks at the property which are by the private dock and may be used by guests (at your own risk). Life vests are also provided. There is no public transport in the area, but parking is provided in the front driveway for 3 cars. There is a yard front and rear and a gas grill is available on the deck. Bedroom 1 has a double bed. Bedroom 2 has a bunk bed with a twin over a double bed. Bedroom 3 has a bunk bed with 2 twins. There is a washer and dryer as well as a 2nd toilet in an attached workshop to the side of the house - which is accessible via a separate locked door from the outside. The NeighborhoodThe house is situated in quiet residential neighborhood with properties along the Chester River. Getting AroundThere is no public transportation to speak of in Chestertown. The best way to get around is by car, although cycling is a great option as the roads are pretty flat in and around the town. Other Things to NotePlease note that cleaning and linens are added on to each booking for $100. Linens includes all bedding and towels.
Home/Apartment
2br Home/Apartment
  • Wifi
  • Parking
The SpaceThe downstairs space has a kitchen, living room and dining area. The 1st floor bedroom has a king-size bed. The living room has a fold out couch. The bathroom has a shower. There are internal stairs which lead to another living/kitchen area. Upstairs bedroom has queen-size bed. The upstairs bathroom has a shower and tub. There is a small deck with a cafe table and chairs on the second floor. Guest AccessGuests have a private entrance on the first floor. There is an outdoor staircase which lead to the 2nd floor. There is also an internal staircase which can be used to reach the 2nd floor. Interaction with GuestsThe owner occupies the apartment next door. She is available to assist during your stay. The NeighborhoodCharming, quiet, safe neighborhood in an historic, college town. Getting AroundA car is necessary if you need to get anywhere outside of the town. You can easily walk anywhere in downtown Chestertown. Washington College is within walking distance. Uber is a new option in Chestertown. Other Things to NoteThere are 2 parking spaces in the private parking lot behind the apartment. There is ample street parking nearby.
house
3br house
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in Chestertown - with views no hotel can match!
    apt. / condo
    1br apt. / condo
      This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a short visit to this charming town. Longer stays are available. There is one parking spot on the premise. Ample street parking is nearby. The apartment is conveniently located in downtown Chestertown. It is close to Washington College and the Chester River waterfront. It is adjacent to the beautiful Memorial Park. It is a wonderful place to stay if you are looking for a weekend retreat in a historic, quaint town on the Eastern Shore of Maryland.
      Bedroom
      Bedroom
      • Wifi
      • Breakfast
      • Parking
      The SpaceWe are a small family farm located in the peaceful countryside of Centreville, Maryland. The house is a single family farm house with all of the modern amenities. Its very quiet here with beautiful sunsets and country views from the front porch rockers. Guest AccessAt this time we have one bedroom available. The bedroom has one queen size bed, dresser and closet space. There is lovely country views from the windows. A full private bathroom is located in the hall, adjacent to the bedroom, and is reserved for guests only. We can accommodate 2 adults in the room. Children are welcome to stay with their parents. There is ample floor space for an airbed, or sleeping bags for the kids. We also have a full kitchen where we will have breakfast available in the morning and coffee and cold drinks anytime. I also offer our farm fresh eggs for sale, and when available, various seasonal produce that is grown here on the farm. There is a backyard with outdoor seating and a firepit for those chilly evenings. There is also a front porch with rockers for relaxing, reading or just gazing at the grazing horses. We have a living room for gathering and relaxing as well as a family room with TV and DVD. Interaction with GuestsWe will be here most of the time. Sometimes I am outside working on the farm, caring for the animals, but I will always be available if needed and/or not.. ;-) We totally understand the need for privacy and we offer a quiet retreat for our guests as well. We also offer breakfast with your stay, and will always be helpful with recommendations for local dining and events. We love the MD Eastern Shore and are always happy to share what makes this area special! The NeighborhoodWe are located on the central Eastern Shore of Maryland. Centreville is about 5 miles away, with a few restaurants and small town shopping. We are also close to the Queenstown Outlets for great discount shopping and Kent Narrows for a nice choice of seafood restaurants and dock bars. Tuckahoe State Park is only a few miles down the road, and offers hiking trails, fishing and kayaking, biking, as well as horseback riding trails. We are also only 1 hour from all the major beaches in Delaware and about 1 hour 45 minutes to Ocean City, Maryland. Baltimore and Washington DC are approximately 1 hour away. Getting AroundWe are in a rural setting, so there isn't any public transportation nearby. A car is a necessity. We are about 1 hour from BWI Airport and about 50 miles to Wilmington, DE where there is an Amtrak station and busses available. Other Things to NotePlease be aware we are a working horse farm. The horses are there for your enjoyment to see, but if you would like to pet or touch them, please let me know and I will be more than happy to introduce you to our 4 legged family. ;-) We have a variety of critters living here, including chickens, a rooster, cats and even a miniature donkey named Henry! If you are a horse owner and also need accommodations for your horse, I can arrange for that as well. Please message me for details.
      Bed & Breakfast
      1br Bed & Breakfast
      • Wifi
      • Breakfast
      • Parking
      The SpaceThe guest room is situated in the manor house of the 1860 National Register Brampton Bed and Breakfast Inn. This very spacious guest room accommodates 2 guests sharing a king bed. The en-suite bath room has a shower with body jets. Included is afternoon tea and a full a-la-carte breakfast in the morning. Guest AccessOur guests have access to all the common rooms and the grounds surrounding Brampton. A complimentary a-la-carte country breakfast is served in our dining room between 8:30 and 10 am. An earlier breakfast to-go can be accommodated on request. Our guests traveling with an electric car have access to our Tesla or Clipper Creek charging stations at no extra charge. Interaction with GuestsWe are always available to help plan a visit to the area, answer questions and help in any way we can. The NeighborhoodThe Brampton is located 1 1/2 mile from the arts and entertainment center of Chestertown, Maryland and is an ideal base to explore all that the Eastern Shore has to offer. Getting AroundBy car only. There is no public transportation available in our area. Other Things to NoteThis is a fully licensed and inspected bed and breakfast. We welcome guests from all over the world.
      Bedroom
      Bedroom
      • Breakfast
      • Parking
      Enjoy a three hour sunset sail on the beautiful Chesapeake Bay. Watch eagles, ospreys, and herons fish for dinner. Spend the night anchored away from civilization, moonless nights expose the Milky Way. Leave your worries on the dock.
      Hotel
      Good
      62 reviews
      2.5-star Hotel
      Situated in Chestertown, this hotel is within 2 mi (3 km) of Washington College, Historical Society of Kent County Maryland, and Garfield Center for the Arts at the Prince Theater. Wilmer Park is 1.7 mi (2.7 km) away.
      Bedroom
      Bedroom
      • Wifi
      • Gym
      • Pets Allowed
      • Breakfast
      • Parking
      • Swimming Pool
      Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the Eastern Shore of the Chesapeake Bay. Great Oak has 12 guestrooms, 15 baths, various common rooms and vibrant sunsets.
      hotels
      73br hotels
      • Breakfast
      • Parking
      • Swimming Pool
      • Wifi
      Located in Chestertown, Quality Suites is convenient to Washington College and Historical Society of Kent County Maryland. This hotel is within close proximity of Garfield Center for the Arts at the Prince Theater and Wilmer Park. Make yourself at home in one of the 53 air-conditioned guestrooms. Satellite television is provided for your entertainment. Amenities Enjoy the recreation opportunities such as an indoor pool or make use of other amenities including complimentary wireless Internet access. A complimentary buffet breakfast is included. Featured amenities include complimentary newspapers in the lobby, laundry facilities, and an elevator (lift). Free self parking is available onsite.
      Home/Apartment
      1br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      The SpaceOriginally designed as an in-law suite, the apartment adjoins the main house but offers total privacy with separate driveway, entrance and a private porch . Consider it your home away from home for a weekend or longer stay. Hardwood floors, comfortable furnishings, cable TV, DVD and VCR, high speed WiFi internet, separate controls for central heating and air conditioning from the eco friendly geothermal system, and tankless hot water. Beautiful water views from the kitchen and living room, a cozy bedroom with ample closet space, a large, fully equipped eat in kitchen with food pantry. The living room has a sleep sofa available for up to 2 children or guests (please contact us for particulars). Pets are welcome. Guest AccessThe entire apartment is yours, with a driveway that allows parking right by the entrance. The waterfront wooded lot has a screened gazebo and garden area, a dock and plenty of space to enjoy the outdoors. The two person kayak is yours to enjoy. You have your own small private dock. Bird watchers will identify many species large and small; Ducks, Geese, Osprey, Bald Eagles, Great Blue Herons, Owls, Gulls, Woodpeckers and more. There is a park with playground equipment for children and a sandy swimming beach a short walk away. Roundtop Park has tennis courts a mile away. The neighborhood is quiet and safe so bring your bicycles, skate boards, scooters and walking or running shoes. Interaction with GuestsWe live in the adjoining house so we are available to assist you if needed. Other Things to NoteHistoric Chestertown and Washington College are a 5 minute drive away, across the Chester River Bridge. The bridge has a pedestrian sidewalk if you prefer to walk.
      Home/Apartment
      2br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      Fully remodeled w/ concrete countertops; washer/dryer; wine bar; plush high-end mattresses on queen beds. Cozy L-shaped couch & recliner in living room. Pet-friendly. Backyard: patio, umbrella table, shed w/ bikes. In heart of quaint downtown.
      Home/Apartment
      Excellent
      8 reviews
      3br Home/Apartment
      • Wifi
      • Breakfast
      • Parking
      This is a very comfortable house on one level with many amenities. Attractively decorated and recently renovated. Located in a quiet neighborhood on the Chester River. Easy walk to Chestertown Historic District, charming shops, Farmer's Market, etc.
      motel
      Poor
      54 reviews
      28br motel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      Situated in Chestertown, this motel is within 1 mi (2 km) of Washington College, Historical Society of Kent County Maryland, and Garfield Center for the Arts at the Prince Theater. Wilmer Park is 1.3 mi (2.1 km) away.
      Home/Apartment
      1 review
      4br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      This two-story historic country house has a wide entrance hallway spanning the length the house & leading to an outside brick patio. A sunny kitchen forms a continuous entertaining space with the dining room. Includes cozy den & formal living room.
      Home/Apartment
      1 review
      5br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      Historic circa 1690 manor house surrounded by several porches. A long lane centers to the front of the house and provides an easy walk to downtown Chestertown or a quick jaunt to the Chester River on the other side of the road.
      Home/Apartment
      1 review
      4br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      A screened front porch provides a perfect dining area with view of river. The back porch leading to the kitchen and pantry provides storage for hunting and fishing equipment. The great room has a window seat gracing the width of the room.
      hotel
      47 reviews
      hotel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      When visiting Chestertown, Quality Suites is a great choice to consider. Guests can take a dip in the indoor pool, and free perks include buffet breakfast and self parking.
      hotel
      81br hotel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      Situated in Chestertown, this hotel is within 2 mi (3 km) of Washington College, Historical Society of Kent County Maryland, and Garfield Center for the Arts at the Prince Theater. Wilmer Park is 1.6 mi (2.7 km) away.
      hotel
      Excellent
      3 reviews
      4br hotel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      Situated in Chestertown, this bed & breakfast is within a 10-minute walk of Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Wilmer Park and Washington College are also within 15 minutes.
      hotel
      47 reviews
      hotel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      When visiting Chestertown, Quality Suites is a great choice to consider. Guests can take a dip in the indoor pool, and free perks include buffet breakfast and self parking.
      hotel
      2br hotel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      Situated in Chestertown, this bed & breakfast is within a 15-minute walk of Historical Society of Kent County Maryland, Washington College, and Garfield Center for the Arts at the Prince Theater. Wilmer Park is 0.7 mi (1.2 km) away.
      Home/Apartment
      2br Home/Apartment
      • Wifi
      • Pets Allowed
      • Parking
      The SpaceThe cottage sits on a quiet pond with ample yard to run and play. There is a brick patio with a gas grill and picnic table to enjoy the outdoors. The kitchen is fully stocked with everything you shoul dneed to make your stay pleasant and relaxing! There is a washing machine and dryer in the cottage for your use during your stay. Guest AccessYou will have full access to the yard, cottage, dock and beach area during your stay. Interaction with GuestsWe are in the main house on the property and will be available at all times either in person or by phone. The NeighborhoodWe are in a quiet neighborhood on the Chestert River. There are lots of great routes to walk, run or bike! There are three bikes supplied for the cottage for the quick ride into to town, about 1 1/2 miles, although many people prefer the walk. There is a great farmers market on Saturday morning for fresh produce and crafts. There are four kayaks which may be used. Life jackets are supplied and are necessary! Getting AroundThere are seceral "taxi" services in Chestertown including Uber. If you need help getting here from the airport or train station please let us know and we will help arrange pick-up and drop-off.
      Home/Apartment
      3br Home/Apartment
      • Wifi
      • Parking
      The SpaceDuring your stay, you'll have access to a 3 bedroom/ 1.5 bath home with an outdoor patio and grill. Start your day with a cup of coffee in our sunroom or enjoy the mahogany floored wrap around porch. Guest Access1 Master Bedroom - King Bed 1 Guest Bedroom - 2 Queen Beds 1 Guest Bedroom - 1 Queen Bed 1.5 Bathrooms Screened-in sunroom with outdoor dining table Gas Grill Renovated Kitchen with dishwasher Washer/Dryer
      hotel
      12br hotel
      • Breakfast
      • Gym
      • Parking
      • Pets Allowed
      • Swimming Pool
      • Wifi
      Located in Chestertown, this beachfront bed & breakfast is next to a golf course and within 9 mi (15 km) of Washington College, Garfield Center for the Arts at the Prince Theater, and Historical Society of Kent County Maryland. Wilmer Park and The Mainstay are also within 12 mi (20 km).
      Home/Apartment
      1br Home/Apartment
        Cet appartement d'une chambre artistique, baigné de lumière se trouve dans l'historique Chestertown, MD. L'espace comprend combo de salle/cuisine, chambre à coucher avec lit queen size, salle de bains avec douche et baignoire. Une terrasse extérieure avec table de café et chaises est un endroit agréable pour s'asseoir sur une journée ensoleillée. Il est parfait pour une courte visite de cette charmante ville. Séjours plus longs sont disponibles. Il y a une place de stationnement sur la prémisse. Stationnement rue amplement se trouve à proximité.
        Home/Apartment
        3br Home/Apartment
          A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in Chestertown - with views no hotel can match!
          Bed & Breakfast
          Bed & Breakfast
          • Pets Allowed
          • Wifi
          One of Maryland's historically significant estates, Great Oak Manor sits on twelve acres directly on the Chesapeake Bay just outside of Chestertown in Maryland's Eastern Shore. With large common rooms, beautifully appointed guest rooms, and comfortable outside seating areas shaded by majestic Oak and Walnut trees, the Manor affords its guests ample and comfortable areas in which to relax.The Manor will meet your every need with 1,200 ft. of waterfront, a private beach and the most beautiful sunsets on the Eastern Shore.
          Bed & Breakfast
          Bed & Breakfast
          • Wifi
          Ahh....the aromas of fresh bread baking, chocolate chip cookies just out of the oven, "scrubbed-squeaky clean" and sheets hung out on the clothesline...Simple. Subtle. The amenities of home. Quiet. 100 yards from Washington College, 10 minute stroll to historic downtown, 15 to the Chester River. Check Tripadvisor Reviews.
          Bed & Breakfast
          Bed & Breakfast
          • Pets Allowed
          • Wifi
          Award Winning Chestertown Inn on 20 acres with unforgettable suites and scrumptious breakfasts! Indulge in the luxuries of modern life at our 19th century antebellum plantation in Chestertown, MD. An historic Chesapeake Bay bed and breakfast offering the luxurious amenities today's traveler deserve: en-suite baths with 2 person whirlpool tubs, body-jetted showers, steam showers, heated towel bars and Japanese style ofuro soaking tubs. Loose yourself in comfy surroundings at our Eastern Shore bed and breakfast with wood-burning fireplaces, fluffy robes, flat screen TVs with DVDs, and free Wi-Fi. Enjoy a memorable a-la-carte gourmet breakfast delivered to your cottage, or served in the formal dining room of our Chestertown, MD inn. Our Chestertown Bed and Breakfast is the ultimate romantic oasis on Maryland’s Eastern Shore, located on 20 wooded acres and gorgeously landscaped gardens. Visit nearby St. Michaels and Annapolis, both an easy 1 hour drive from our romantic Maryland getaway. Our Chesapeake B&B was the only Bed and Breakfast in Maryland selected by National Geographic Traveler for it’s first-ever, annual “Stay List”. The editor’s list included just 150 properties in the United States, Canada, and the Caribbean. When searching for romantic cottages in Maryland, a Chesapeake Bay inn, or an Eastern Shore bed and breakfast, there is one clear choice, The Brampton Inn.