Search accommodations in Chestertown, MD

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.

Harbor View Haven is a waterfront property situated in Chestertown, Maryland, just a short drive from the historic town centre.
This spacious house boasts three bedrooms and two bathrooms, sleeping up to ten guests, and features a private dock, a hot tub, a fully equipped kitchen, and a game room with a ping pong table.

This Chestertown holiday home is situated within a 2.4km walk of Kingstown Park, the Historical Society of Kent County Maryland, and the Garfield Center for the Arts, with Washington College and River Arts Chestertown also within 1.6km.
The 134 square metre property boasts three bedrooms, three bathrooms, sleeps six guests, and includes a fully equipped kitchen, free Wi-Fi, a private patio, and is within walking distance of several attractions.

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 Chestertown residence is a 14-minute walk from the Kent County Historical Society and a 15-minute walk to Wilmer Park, offering convenient access to local attractions.
This 90 square metre holiday home accommodates up to six guests, featuring two bedrooms, two bathrooms, a private garden, a terrace, barbecue facilities, and on-site parking.

This dog-friendly residence in Chestertown is situated within walking distance of the historic town centre, with New Castle Airport located 72 kilometres away.
This property offers 90 square metres of living space, accommodating up to 11 guests with two bathrooms, air conditioning, complimentary WiFi, and on-site parking, plus a fully equipped kitchen.

This Chestertown cottage, located 2.4 kilometres from Washington College and 6.8 kilometres from Rolphs Wharf Marina, offers easy access to Betterton Beach and Rock Hall Harbour within a 26-kilometre radius.
This pet-friendly holiday home boasts 4.5 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a garden, free parking, and free Wi-Fi, perfect for a relaxing getaway.

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 Chestertown apartment, centrally located within a 0.6km radius of River Arts Chestertown, the Garfield Center for the Arts, and the Historical Society of Kent County, Maryland, offers easy walking access to cultural attractions and Wilmer Park.
The 48 square metre flat features one bedroom, one bathroom, sleeps two guests, and includes a kitchenette with fridge, freezer, and microwave, plus a private fenced yard, balcony, and free Wi-Fi.

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 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 one-bedroom apartment is conveniently located in Rock Hall, within a short walk of Ferry Park and Waterman’s Museum, and within a 2-mile radius of Rock Hall Harbor and The Mainstay. Guests have consistently rated this property excellent for location, cleanliness, and overall experience.
The apartment offers 74 square metres of space, comfortably accommodating up to three guests. The well-equipped kitchen, private balcony, and convenient amenities such as free Wi-Fi, parking, and barbecue grills ensure a comfortable and enjoyable stay.