Search accommodations in Chestertown, MD

This apartment is situated in the heart of Chestertown, just a short walk from Washington College, the Chester River and the town's historic district, with easy access to shops and restaurants on High Street. The apartment has received excellent ratings for location, cleanliness and overall experience.
This spacious property spans two levels and offers four bedrooms, comfortably accommodating up to eight guests. The apartment boasts a fully equipped kitchen, air conditioning, a garden and parking, ensuring a comfortable and enjoyable stay.

This private waterfront cottage on Langford Creek is a short drive from Chestertown's downtown amenities, including restaurants, shops, and its farmers market.
This 3-bedroom, 2-bathroom dwelling accommodates up to 6 guests and features a well-equipped kitchen, air conditioning, a Jacuzzi, garden, parking, a private deck with a hot tub, an outdoor shower, and a private pier with a boat slip.

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 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 3-bedroom flat is located in a quiet Kingstown neighbourhood, offering excellent birdwatching and a short 3-kilometre drive to the central business district.
Guests can enjoy a wood-burning fireplace, a private garden, and keyless entry, with amenities including WiFi, air conditioning, and on-site laundry facilities for up to 4 people.

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 Chestertown carriage house, situated at the rear of a Victorian property, offers a peaceful retreat a short walk from the town centre.
The property comprises a fully equipped kitchen, modern bathroom, and private garden with covered parking including EV charging; sleeping two guests, it provides all linens and towels.

This charming apartment is situated in the heart of Chestertown's historic district, just a short walk from the town's bustling restaurants, shops, and the picturesque Chester River waterfront. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a well-equipped kitchen with modern appliances, a spacious living area, and a private outdoor space with a covered porch and a pergola, perfect for relaxing and enjoying the beautiful surroundings.

This charming 3-bedroom apartment is situated in the historic district of Chestertown, just a short walk from the bustling High Street and two blocks from the picturesque Chester River. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers ample space for families or groups of friends, with three bathrooms and a capacity of six guests. Enjoy modern amenities such as a fully equipped kitchen, a washer and dryer, a gas fireplace, and a private garden with a screened porch and a brick terrace, perfect for relaxing evenings.

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 apartment is located just a block from the waterfront in Kingstown, within walking distance of shops, galleries, and restaurants, offering a peaceful retreat in a quiet area of Chestertown. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
This home, a charmingly renovated "American Four Square" style house, can accommodate up to seven guests and offers full use of the first and second floors. The property features a fully equipped kitchen, comfortable bedrooms with high-quality mattresses, air conditioning, a garden, parking, and internet access.

This property is located in Chestertown, within 500 meters of its dining, shopping, and waterfront attractions, and close to the Saturday Farmers Market.
This three-bedroom, one-bathroom flat accommodates up to six guests and features a well-equipped kitchen, air conditioning, a garden, and a screened-in porch.