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68 Rentals · Chestertown
68 Rentals · Chestertown
Open flow design of windows and doors of main floor of the home runs right out into the garden and pool. Stunning views. 3 block walk from all of town's adorable amenities. Sun room off of master accommodates blow up bed for 2 additional guests. Learn More
The master suite has a queen bed and a large sun room with a twin day bed. There is also a queen blow up mattress for that space. The second bedroom has a queen bed. The house is fully, tastefully, and comfortably furnished. Flatscreen HDTV and wifi. Salt water pool and beautiful garden setting. Screened in porch overlooking pool and garden. The entire house, garden, and pool is rented to a guest with a booking for this property. Feel free to text, call, or email with any questions...
This cozy one-bedroom house is a wonderful spot for an Eastern Shore adventure. Enjoy this cottage for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Great nature, bird watching & sunsets. Learn More
The one-bedroom house includes full kitchen, living room, bedroom with queen-size bed and a screened porch and patio. The living room has a sleeping alcove with 2 single beds. Full bathroom with shower and tub. A 15 minute drive from historic Chestertown, MD and 10 minutes to the bayside town of Rock Hall. Twenty minutes to Eastern Neck Island Wildlife Refuge. Enjoy nature, birds - bald eagles, ospreys, blue herons - and more by the bay. Conveniently located 90 minutes from Baltimore, Wa...
Located in historic downtown Chestertown. One block from river, walking distance to bakery, restaurants, coffee shops, book store, retail shops and Saturday's Farmer's Market. Learn More
Spending 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 of 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...
Lovely home with great indoor-outdoor entertaining space. Fully renovated 3 bed, 2.5 bath. Top of the line open floor plan kitchen/family room. Located in Historic district on the main street only few blocks from restaurants, shops and river front. Learn More
Combing 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...
Perfect place to relax by the river, with sunsets directly over the dock, you'll love the view. Learn More
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! Chestertown is a quaint historic town on the Maryland Eastern Shore and boasts unique shops, restaurants as well as supermark...
Located 7 miles to the center of historic Chestertown the county seat of Kent County, Maryland. This vacation rental has a private salt pool with a half acre pond, 4 bedrooms 3 baths. Very peaceful & private surrounded by nature. Learn More
Lovely home in a very quite setting, two master suite's, great salt pool & and two charcoal grills The entire house and pool We will greet you upon arrival to answer any questions. We are a phone call or text away for any additional questions about the house or the area. Very quite road with a very old church Saint Paul's at the end of the road one of the oldest churches in the area, Tallulah Bankhead is buried on the church yard grounds . wonderful biking trails and a runners paradise ...
This wonderful one-bedroom apartment is located near downtown historic Chestertown & Washington College. The apartment can accommodate 4 guests. It is the perfect pied-à-terre for enjoying this historic, artistic town on Maryland's Eastern Shore. Learn More
The space includes kitchen/living room combo, bedroom with queen size bed. An air mattress can be set up in the living room for 2 additional guests. 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 Wa...
Located in the heart of historic Chestertown, our pet-friendly house has loads of charm -- and yet is comfortable and contemporary. There's a fenced in yard and you're an easy block and a half away from downtown & waterfront. Learn More
Our two bedroom, two bathroom house, built in the 1880s, is sprawling and spacious, with a pretty front porch and a cozy backyard with firepit, woven wicker-like chairs, and a gorgeous and shady magnolia tree canopy. Inside, our living room has a brand new sofa bed (sleeps two) and leads into the dining room. Both have beautiful antique slate fireplaces that, alas, are non-working at present (we have plans to change that). There's a bathroom with shower. The kitchen is fully equipped with t...
This wonderful 2 Bedroom/ 2 Bath Duplex is located near downtown Chestertown and Washington College. It is an ideal place for enjoying the historic, artistic, college town on Maryland's Eastern Shore. It accommodates 4 to 6 guests comfortably. Learn More
The downstairs space has a kitchen, living room and dining area. The 1st floor bedroom has a king-size bed. 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. Fold Out Couch or Air Mattress can be set up for additional beds Guests have a private entrance on the first floor. There is an outdo...
A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 3 guests. It is the perfect pied-à-terre for enjoying this historic, artistic town on Maryland's Eastern Shore. Learn More
The 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, qua...
Nestled 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...
This nice modern, very clean, efficiency that has everything you need. Nicely furnished including a double bed and a couch with pull out bed. It has a full bath with tub/shower. There is a fully equipped kitchen with oven, microwave, full size fridge, coffee pot, dishes and cookware. Learn More
Please be aware that this is a studio, which is an "open concept" space. It is like a luxury hotel suite. If there are more than two in your party, and you will be using the pull out bed in the couch, you will NOT have privacy, as it is all in the same space. It is a nice large space, but there are no walls separating the sleeping areas. There is an outdoor screened-in area with fireplace for your picnics. We are located in a beautiful rural area and this is great location to explore the ...
Welcome to Hope Found Farm. We are a small, family owned horse farm located in beautiful Centreville, Maryland. If you are looking for peace and quiet but also wish to be within 1 hour from DC, Baltimore and the beaches, you have found the place! Learn More
We 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. At 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 rese...
Our Beautiful Annapolis Waterfront, Master Bedroom Suite, on the Little Magothy River is a wonderful vacation spot for the perfect Retreat! You'll love the location, the pool, the beautiful views in every direction, and all the local birds. Learn More
Master Suite with cathedral ceiling, king size bed, private master bath, private entrance, sliding doors onto large deck overlooking the pool and 500 ft of waterfront!! Located on the Little Magothy River in Annapolis and 10 minutes to downtown. In warm weather this is the perfect location for swimming, kayaking, fishing, crabbing and water sports. Sunbathe by the pool, or grill on the gas grill and enjoy your meal on the deck under the umbrella, surrounded by potted flowers every...
Chesapeake Bay room for rent for Commissioning Week. Directly on the Chesapeake Bay in a working Lighthouse. Six(6) miles from the Naval Academy in Beautiful St. Margarets. 300ft pier and Huge deck. Call 410.757.7388 Learn More
This brand new home is only 8 minutes to downtown Annapolis. Enjoy an open concept with bright natural light and gorgeous kitchen island with a fully stocked kitchen. Both rooms have queen beds and their own baths. We are the perfect home for your vacation needs. Learn More
Fully stocked kitchen Wall mounted TV with movie channels Large reading room 2 queens beds 2 baths Second TV and rec room in basement Private and common yard space 2 night minimum please
Wonderful peaceful place. We are open to everyone. Come and visit. Would love to meet you. Learn More
Bedroom and private bathroom. Big open front porch and screened back porches for sitting, quite wooded family neighborhood, 7 minutes from downtown Annapolis, 5 minute walk to the water, 5 minute walk to Broadneck park. Includes wireless. We have a special place. With a lot of positive energy. We are here to welcome all that have the want to travel and meet new people. I love the water and it is very close. Many weekends I may be out sailing. We have a cat but he is kept out of ...
One bedroom in a cute beach cottage in beautiful Annapolis. Internet/ Cable / Chromecast / Netflix / Washer dryer/ Treadmill/ Community beach access/ New Temperpedic type mattress/ Hardwood floors and fireplace Great location! Learn More
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