Chestertown 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.
      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
      • Gym
      • 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
      2 reviews
      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
          Une maison de 3 chambres sur la rivière de Chester avec d'incroyables couchers de soleil sur le quai. Entièrement équipées, avec air climatisé central, lave-vaisselle, laveuse, sécheuse et stationnement - libre aussi utilisation des kayaks pour profiter de la rivière de Chester. Une propriété idéale pour ceux qui dépose, ramasser ou simple visiteur étudiant au Washington College à Chestertown - avec vue sur qu'aucun hôtel ne peut correspondre !
          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.
          Country House
          1br Country House
          • Wifi
          • Breakfast
          • Parking
          My place is close to Great Oak Landing (marina). You’ll love my place because of the outdoors space, the comfy bed, the light, and the neighborhood. My place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets).
          Farm Stay
          5br Farm Stay
          • Wifi
          • Pets Allowed
          The SpaceThe lovely restored and updated colonial farmhouse features 5 very comfortably sized bedrooms. Two rooms feature en suite baths and there is a third floor bunk room for the kids. Prepare family meals in the gourmet kitchen and gather everyone to eat in either the large dinning room or the outside eating area located in the shade of the pergola. Nature abounds at Oxbow Farm. Take long walks or bike rides on the farm lane or glide down Upper Creek in a kayak. With plenty of outdoor seating there`s really no reason to stay inside on warm sunny days. For the shopper the shops of Chestertown are only a few moments away. Feel the stress begin to wash away by booking your Oxbow Farm vacation today!! Guest AccessInterior: Towels and bed linens included Wireless Internet (for web browsing and email use only) Flat Screen TV for DVD`s Only Wood burning fireplace (wood not provided) Gourmet Kitchen Washer/Dryer En Suite Bathrooms Exterior: Fire Pit 3 Bicycles Charcoal Grill Outdoor Dining Interaction with GuestsProperty is professionally managed Getting AroundCar is necessary, there is no public transportation and limited taxi/uber service. Other Things to NoteCleaning fee includes bed and bath linens and beds made upon arrival. Please contact us for exact quote, pricing does not reflect all combinations of seasons and lengths of stay.
          Home/Apartment
          4br Home/Apartment
          • Parking
          • Pets Allowed
          • Wifi
          Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore. Experience the beauty of the Chester River from this secluded farm located minutes from historic Chestertown and Washington College. This 400 acre vacation rental sits on the Chester River and features both a pond and a private forty foot pool. There is easy access to fishing in the pond or on the river and kayaking or canoeing from the private dock. An ideal family vacation spot, spend your days relaxing by the pool, walking miles of farm trails and playing on the river. Resident wildlife includes Bald Eagles, Osprey, Deer and Wild Turkeys. Bring your bike and enjoy Kent County's beautiful, flat country roads. Watch the sunset from the deck or screen porch overlooking the pool, pond, river and corn fields. Experience historic Chestertown which offers restaurants, shops, and a wonderful farmer's market on Saturday mornings. Experience nearby Rock Hall (crabs on the deck at Waterman's are not to be missed) and the Eastern Neck Wildlife Refuge. Our tastefully decorated house is perfect for one or two families. There are two master bedrooms each with queen beds and private baths. There are two additional bedrooms each with two twin beds and private baths. We provide linens and towels. The upstairs great room, leading to a deck and screened porch, offers spectacular river and farm views and a cozy first floor den provides a second gathering space. The dining room seats eight comfortably and the spacious well out fitted newly renovated kitchen makes it easy to cook for a crowd. We provide linens and towels. The kitchen is fully equipped. We welcome families and pets. We ask only that you treat our house as you would your own. Eagle Point Farm is place where memories are made. Come for a visit. Return again and again. Keywords: Farm, Eastern Shore, Waterfront House, Chester River, Chestertown, Maryland, Country, Wildlife, Secluded, Pool, Dock, Washington College, Queenstown Outlets, Fishing, Maryland Crabs, Rock Hall, Chesapeake Bay, Wifi, Internet Access, Outlet Shopping, tastefully decorated
          Home/Apartment
          2br Home/Apartment
          • Parking
          • Pets Allowed
          This property offers spectacular views of the Chester River from the Family room, Kitchen, & Dining room, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 2 large bedrooms(queen beds.)One has views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa & has the best view of the river. The family room features hardwood flooring, wet bar w/wine cooler, recessed lighting and decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are french doors from the dining area that will go out to a large deck that has a cushion patio set. There is a laundry area that includes a stacked washer & dryer. Both bathrooms have also renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. There is also a shared launch(must use 4 wheel drive b/c it is not concrete.) Bar-B-Que grill, (propane not guaranteed) hammock and patio set as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available upon request(pls note,we do not have children's life vests.) There is also a fire pit for those cool nights or to just hang out and make smoors. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 20 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown. ** Some dates to consider for fun filled family weeks in 2017 season Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. Bettertown days @ Betterton Beach usually the fist weekend in Aug The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. Sultana down rigging late Oct early Nov, early Oct is Rock Hall's Fallfest. Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know. Feel free to surf the web as well. Most of the local towns have event calendars you can find online. Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. The neighbor has two labs that are very friendly and may come over to greet you. We have two small dogs as well that also like to say hi on occasion. FYI, the school zone has camera 24/7, so watch your speed.
          Hotel
          4br Hotel
          • Parking
          • Pets Allowed
          • Wifi
          The River Lodge sits on the scenic Chester River located 5 miles outside of Chestertown. It's the perfect little get away. You'll experience beautiful sunsets and tranquil nights. During the day sit in a chair on your small private beach and bask in the sun rays. Fish off the dock, swim in the river, play ball in the large yard, and at the end of the day enjoy a delicious meal on the porch that was cooked on the BBQ grill. There are hardwood floors through out the lodge. Twin beds in all the bedrooms with the exception of one that has a queen bed and a day bed. The River Lodge offers a great rustic setting for a family gathering, hunters, or a guys weekend. The property lends itself to many possibilities such as crab feasts, picnics, outdoor weddings, family reunions, etc. The River Lodge has a spacious living room with a wondrous view of the Chester River. Keywords: Lodge
          Home/Apartment
          2br Home/Apartment
            Located 18 minutes from charming historic Chestertown, Maryland, Mill Creek House is a contemporary waterfront house with dock. Bald eagles and herons fly overhead, plus it's on the route of thousands of Canada geese. Wildlife abounds! Perfect for a family vacation or a personal reflective getaway. Awesome dock and couple of minutes for the historic city of Chesterton. The home is 2 bedroom, 2 bathroom.
            Home/Apartment
            5br Home/Apartment
            • Parking
            • Wifi
            My home will rent for $650per night. Price negotiable for long term rentals. The home has an incredible view of the Chester River. There is a dock, but the lift is not available for renters. However, there is plenty of room and a piling for your boat. There is a great, newly redone, screened in porch off the master BR and living room. Additionally there is a great room with kitchen, TV area and dining room. There is also a powder room just off the TV area. In the Master BR area there are 2 separate full baths and a walk in closet. Upstairs there are two BRs with 2 twins in each and these share one full bath. Also upstairs there is a large separate BR with a King bed and full bath (bath tub with a shower spray; you can't stand up and take a shower because of a slanted wall. A one car garage is available. There is a lovely meandering driveway leading to my home on the Chester River. There is a wonderful screened porch which overlooks a beautiful lawn and the dock. Guests should also bring their bikes. Kent County roads are built wide to handle farm machinery. Many have bike lanes. Others are lightly traveled and popular with cyclists. Nearby is the village of Rock Hall and Eastern Neck National Wildlife Refuge. You can rent crabbing boats by the bridge near the entrance. Lots of hiking trails. It is home to some of the few remaining Delmarva Fox Squirrels. Rock Hall has several lively waterfront bars. Chestertown hosts a fabulous weekend farmer's market. Artisan bread at Evergrain Bread Company is a must or if you need a night out there are several charming restaurants. Again, the view is just wonderful!!
            Home/Apartment
            3br Home/Apartment
            • Parking
            • Wifi
            Located on renowned Water Street within Chestertown’s historic district, this early 1900s row house has views of the picturesque Chester River, historic Hynson-Ringgold garden and stately 18th and 19th century mansions. Just steps from the town center, dock, and marina—and surrounded by some of the finest historic architecture in Maryland—you can park your car in our private drive and discover all Chestertown has to offer. Stroll brick-lined streets that take you back to the time of George Washington or visit Chestertown’s many contemporary specialty shops, galleries, cafes and fine restaurants. Enjoy a variety of cultural and historic events at Washington College or take in a live performance at the Prince Theater. Want to get out on the water? Book a sail on the historic schooner, Sultana, berthed within view of your house or take a dinner cruise on the riverboat, Packet, departing just steps from your back garden gate. For nature lovers eager to explore the quiet river or countryside, rental kayaks and bikes are available a short walk away. Many of Chestertown’s special events occur right outside your door, including the spirited Tea Party Festival, renowned Chestertown Jazz Festival and popular “Downrigging Weekend.” Don't miss the farmer and artisan’s market every Saturday or fun First Friday’s each month. "Chestertown is a treasure hidden in plain sight," said Richard Moe, president of the National Trust for Historic Preservation. "A small, historic and relatively unspoiled Eastern Shore town, Chestertown had the good sense to hang on to what makes it so special. The result is a vibrant community that offers travelers an ideal retreat." This three-story, three bedroom row house is comfortably furnished with everything you need to enjoy your stay, including a fully equipped kitchen. Situated behind the town’s riverwalk and directly next to a historic garden, it’s a private oasis where natural light fills every room. Relax on one of three porches. Two rear porches offer both sunrise and sunset river views, while a front porch invites you to sit and indulge in a favorite Eastern Shore pastime—watching the world go by.
            Bedroom
            2br Bedroom
            • Parking
            Relax in this immaculate 2 bedroom end unit townhome complete with a second floor balcony off the kitchen where a cup of coffee, tea or cocktail can be enjoyed. The main living area is on the second floor with the bedrooms located on the top floor. The spacious master bedroom has an en suite bathroom with full-size soaking tub. The second bedroom, which sleeps 4, has a private full bath immediately next door. Clean linens are provided. Enjoy the comfortable family room with a variety of games. You may want to set up a puzzle on the coffee table or just prop up your feet. Due to homeowner bylaws, the owner is inconspicuously on ground floor level to quietly manage your stay and provide a freshly-prepared breakfast, if guest desires, each morning; think shore/beach house meets B&B. Kitchen table seating can accommodate up to 6 and a comfortable breakfast bar will sit four. Outdoor balcony bistro dining in the morning and bird watching are also available. You are within walking distance of Washington College, Fountain Park, shops and restaurants. Chester River recreation and miles of scenic roads are beckoning short and long distance bikers and running enthusiasts. When you arrive, the attached garage is a safe place to store your bikes, strollers, kayaks and SUP. I look forward to meeting you and making your stay comfortable!
            Estate
            4br Estate
            • Parking
            • Swimming Pool
            • Wifi
            Highfield Manor is the perfect location for your romantic wedding and reception, corporate event, or vacation with family and friends. Nestled amongst towering great oaks and rushing streams, Highfield Manor offers guests luxurious living, breathtaking views of Whitehill Pond and a relaxing indoor pool and sauna....all just minutes from the Chesapeake Bay. Our guests can enjoy al fresco dining on the many stone terraces and wrap-around balconies. Later, take a stroll along Whitehill pond, and enjoy its lovely fountain and wooden float. Hike across running streams via quaint wooden footbridges to explore the 25 acres of flora and fauna. Relax by the serene koi pond, with playful frogs and turtles, and a beautiful stone waterfall. Once indoors, you'll be greeted with a stylish yet comfortable modern estate home. The living and dining areas are anchored by a large wood-burning fireplace. For the musician, an ebony baby grand piano sets off the unbelievable panoramic view of Whitehill Pond and beyond. Floor-to-ceiling windows create an atmosphere of living in the sky! A mix of mid-century modern and circa-1930 French salon furniture nicely complement the original artwork and modern architectural details of the home. Just ahead is every gourmand's dream; a custom kitchen featuring a Viking stove, double oven, Sub-Zero refrigerator, Jenn-Aire warmer, wet bar, granite countertops and a large butcher-block island. You can prepare an intimate dinner for two or a feast for many...Bon Appetit! Next, walking up the open staircase, you'll discover the master bedroom, with king bed, built-in cabinets, ensuite bathroom and a balcony overlooking the property. The balcony is a perfect spot to enjoy your morning coffee or an evening cocktail. Each tastefully decorated bedroom on this level has a wood-burning stove (non-operational) and plenty of storage. Bedroom 2 also has a balcony and a queen bed, as well as an ensuite bathroom. Bedroom 3 has a full bed and an ensuite bathroom. Next, walk up the open staircase to the bonus bedroom, with treetop views, twin beds and cable/wifi flatscreen TV. This spot has been called the highest point in Kent County. What views! Another fabulous feature of Highfield Manor is the indoor spa located on the lower level. Relax and de-stress in the built-in sauna and eight-person Jacuzzi. For your convenience, the spa area includes a large shower and powder room. Once you leave the spa you can relax in the nicely appointed entertainment room, featuring a large flat-screen TV, queen sleep sofa, poker/backgammon table and walk-out deck. Just steps away, Highfield Manor also includes a detached enclosed pool house featuring an Eternity Pool* and 5-bay carport. Access to the pool and parking is included in your Highfield Manor rental. Due to safety and security concerns, children under ten years old are not permitted at Highfield Manor. Events for more than 10 persons will incur an additional fee, and must be pre-arranged with and approved by the management. Highfield Manor's unique architecture and natural setting is often compared to the modern classic estate Fallingwater. We hope you'll enjoy your stay, and choose to visit Highfield Manor time and again when on Maryland's beautiful Eastern Shore. * The Eternity Pool is NOT AVAILABLE November-March. The Indoor Jacuzzi is available for your use during this period.
            Home/Apartment
            3br Home/Apartment
              Home away from home. This beautiful Victorian has the traditional wrap around porch with rocking chairs and a gourmet kitchen with stainless steel appliances. The master has a unbelievable comfortable king size bed. The other big bedroom has 2 queen size beds in it, just as comfortable. The third bedroom has a queen size bed. This Victorian is in walking distance to Washington College and all the shops and pubs in town. You won't want to leave.
              Cottage
              3br Cottage
              • Parking
              • Pets Allowed
              You can rent this adorable cottage that has the best of every world. This property is located just 2 short miles from historic Chestertown but, situated in a country setting on a deep creek (Morgan creek) with over 2 acres of privacy. The house is 1200 sq. ft. that includes a living room, 1 bathroom, 3 bedrooms, large kitchen with a breakfast bar and full dinning area, stacked washer & dryer. The house has hardwood flooring and newer windows. A swing in the big Maple tree out back for two. A fire pit installed out back for those chilly nights or making smoors. The shed out back has been converted into a game room equipped with ping pong table( was donated to the cause) cards & various board games. There is a 40’ dock with a 10 X 20’ “L” head that is great for boating, cat fishing(really big ones in there,) swimming, or just plain hangin’ out with a cool drink. The water is approximately 19’ at the end of the dock. Children & dogs are welcome. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover track. We are also 20 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown. ** Some dates to consider for fun filled family weeks in 2017 season Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. Bettertown days @ Betterton Beach usually the first weekend in Aug The second weekend in Aug is pirates weekend in Rock Hall another great time to be had. Lots of people dress up for the event. Sultana down rigging late Oct early Nov, early Oct is Rock Hall's Fallfest. Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know. Feel free to surf the web as well. Most of the local towns have event calendars you can find online. Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. FYI, the school zone has camera 24/7, so watch your speed.