Places to stay in Chestertown, MD

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 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 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 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 Chestertown holiday home, located less than 1.6km from Kings Town Park and under 3.2km from the Garfield Centre for the Arts and Wilmer Park, offers convenient access to Kingstown's cultural attractions.
The 300 square metre property boasts a spacious layout with four bedrooms, five bathrooms, and ample room for up to fourteen guests, featuring a private pool, fully equipped kitchen, and outdoor amenities including a terrace and garden.

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 charming house is situated in the heart of Chestertown, just 0.4 kilometres from Washington College and 0.6 kilometres from the waterfront, offering easy access to the town's attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house provides guests with access to the entire property, comfortably accommodating up to four guests. This spacious home features a fully equipped kitchen, a private garden, a fitness centre, and parking, ensuring a comfortable and enjoyable stay.

This Chestertown house, a five-year-old rancher, is conveniently located within walking distance of Washington College and Chestertown's town centre.
Sleeping up to 10 guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen with dishwasher, a garden with Weber grill and Solo Stove fire pit, four televisions, central air conditioning and heating, and ample parking; numerous consumables are provided.

This studio flat is a secluded retreat in Chestertown, offering over 0.4 hectares of private gardens and convenient access to local attractions.
This romantic hideaway accommodates two guests and features a king-size bed, a well-equipped kitchenette with a two-burner hot plate and microwave, a fireplace, and an in-unit washer and dryer, with pets welcome and private parking provided.

This Chestertown apartment is situated just a short walk from the town centre, offering easy access to shops, restaurants, and historical landmarks. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a spacious layout with three bedrooms and a bathroom, comfortably accommodating up to four guests. You'll also enjoy amenities such as a kitchen with a fridge and microwave, air conditioning, a garden, parking, and a private balcony with stunning water views.

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 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.

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 charming flat in Chestertown is ideally located within walking distance of the town's main attractions, offering easy access to shops, restaurants, and historical landmarks. The apartment has received excellent ratings for cleanliness, location, and overall user experience.
The flat is spacious and well-equipped, featuring a large living room, two dining areas, and a laundry room. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking.