Search accommodations in Chestertown, MD

This five-bedroom apartment is situated in a secluded location, just a short drive from the heart of Kingstown, offering peace and quiet in a tranquil setting. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The spacious property can accommodate up to 16 guests, providing ample room for families or large groups. Guests can enjoy a range of amenities, including a private saltwater pool, a hot tub, a fully equipped kitchen, and a garden with a fire pit and outdoor seating, perfect for relaxing and enjoying the beautiful surroundings.

This waterfront estate in historic Chestertown, Maryland, offers direct access to the Chester River and is just minutes from the town's historic district, providing a secluded retreat with extensive natural beauty.
This spacious apartment accommodates up to eight guests, featuring a private garden, swimming pool, and parking, with air conditioning, internet, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, ideal for family holidays or group getaways.

This charming apartment is located just 500 metres from Washington College and a 1.5 kilometre walk from Chestertown's historic downtown, offering easy access to the town's attractions and amenities. The property has consistently received excellent ratings for its location, cleanliness and overall user experience.
The apartment is a three-bedroom, two-bathroom property that can accommodate up to six guests. It features a fully equipped kitchen, air conditioning, a garden, and parking, as well as access to a range of outdoor activities within a 20-kilometre drive.

This charming apartment is situated in the heart of historic Chestertown, just a short walk from the town's shops, restaurants and Washington College. It has received excellent ratings for its location, cleanliness and overall user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It is well-equipped with modern amenities, including a fully fitted kitchen, high-speed internet, air conditioning, a private garden and parking.

This four-bedroom house is situated in a peaceful residential area, approximately 77 kilometres from New Castle Airport. The property offers a spacious 300 square metre layout, accommodating up to 27 guests and featuring amenities such as a swimming pool, garden, and private parking.

This apartment is located in Chestertown, a short distance from Washington College and Rolphs Wharf Marina, offering easy access to cultural attractions and scenic waterfront views. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience.
This self-catering home can accommodate up to three guests and offers a comfortable living space with a bedroom, a bathroom, and a fully equipped kitchen. The apartment comes with a range of amenities, including a private pool, a fitness centre, a spa, and a terrace, perfect for relaxing and enjoying the surrounding area.

This five-bedroom, three-bathroom holiday home in Chestertown, Maryland, boasts a waterfront location, a 43km drive from Rock Hall Harbour and a 45km drive from Rolphs Wharf Marina.
Sleeping nine guests, the property offers a fully equipped kitchen, swimming pool, garden, free Wi-Fi, and on-site parking; nearby activities include boating and kayaking.

This 1-bedroom property in Chestertown, Maryland, offers convenient access to Washington College and the historic town centre, situated just a few hundred meters from the Saturday Farmers Market, boutique shops, and local restaurants, with the scenic Chester River also nearby.
This 1,200+ sq. ft. accommodation provides a private entrance, a kitchenette, and an in-unit washer/dryer, with guests able to enjoy shared access to a swimming pool, garden, barbecue, and firepit, accommodating up to five people.

This 140-acre farm, situated in Worton, Maryland, is adjacent to Still Pond Creek and 13km from Chestertown, offering easy access to the town's farmer's market and shops.
The restored dairy barn provides sleeping quarters for eight guests, boasting recreational facilities including a pool table, foosball, and access to Still Pond Creek for swimming and canoeing (seasonal).

This Chestertown waterfront house, a 1.6km stroll from the Historic District, offers direct access to the Chester River with a private boat dock.
Sleeping up to 14 guests, the spacious property boasts four bedrooms, four bathrooms, a sunroom, a games room, kayaks, canoes, two grills, and a private seasonal outdoor pool (15 May – 15 September).

This apartment is located on the Chesapeake Bay in Betterton, Maryland, just a short drive from the charming town centre. It has excellent user, location and cleanliness ratings. The apartment offers spacious accommodation in the main house and guest house, each with three bedrooms and two bathrooms. Amenities include a private sandy beach, a heated swimming pool, a hot tub, a 150-metre pier, and a large garden.

This renovated duplex offers a prime downtown Chestertown location, mere steps from dining, shopping, and waterfront views.
This 93-square-meter dwelling sleeps four, featuring two bedrooms, one bathroom, and a fully equipped kitchen, with grip bars on the staircase for added accessibility.

This three-bedroom apartment in Downtown Chestertown is just a short walk from the town's shops, cafes, and restaurants.
The apartment, spread over two floors, comfortably accommodates seven guests and features a fully equipped kitchen, two bathrooms, and free on-street parking.

This apartment is located on the first floor of a building just a short walk from the bustling downtown area of Chestertown, Maryland, offering easy access to shops, cafes, and restaurants. The property enjoys excellent user, location and cleanliness ratings.
The apartment has two bedrooms and one bathroom, accommodating up to four guests. The fully equipped kitchen, private patio and shared front porch provide everything you need for a comfortable and enjoyable stay.

Stepne Manor is a five-bedroom house situated in the historic district of Chestertown, Maryland, a short walk from Fountain Park, the Chestertown Marina, and Wilmer Park on the Chester River. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The house comfortably accommodates 15 guests and features a private suite with a Jacuzzi tub. Guests can enjoy a range of amenities including a garden, a terrace, and a spa, as well as modern comforts like air conditioning, satellite TV, and a fully equipped kitchen.

This seven-bedroom, five-and-a-half-bathroom house is situated on Greys Inn Creek, approximately 11 kilometres from Rock Hall town.
Sleeping up to 18 guests, this waterfront property boasts a private dock, kayaks, paddleboards, a fire pit, and is pet-friendly (up to two dogs, maximum 45kg).