Best apartment offers in Chestertown, MD

This luxurious waterfront property, situated 1.6km from Chestertown's town centre and adjacent to the Chester River Yacht & Country Club, offers stunning water and golf course views.
The 167 square metre home boasts three bedrooms, three bathrooms, and sleeps eight guests, featuring a fully equipped kitchen, air conditioning, and access to a garden; wildlife viewing opportunities abound.

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 newly furnished one-bedroom flat in Chestertown, available from mid-April 2026, offers guests the chance to be among its first visitors following its conversion to short-term rental, with specific district and landmark proximity to be confirmed post-renovation. This pet-friendly apartment includes a kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and accommodates up to two guests, providing a fresh base for exploring the town.

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.

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 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 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 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 magnificent 6-bedroom manor house, situated on a 325-acre farm six miles (approximately 9.7km) outside Chestertown, Maryland, on Morgan Creek, offers a tranquil escape near Kingstown.
The 557-square-metre property boasts a private pool, spa, and extensive grounds including walking trails, a vineyard, and shoreline access, alongside concierge services such as a private chef and daily housekeeping.

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 semi-detached house is situated in Chestertown, Maryland, less than 0.8 kilometres from Washington College and 2.4 kilometres from the town centre.
This modern three-bedroom property, suitable for up to six guests, features a fully equipped kitchen, a private garden with a covered patio, and a comfortable living area with a 50-inch television.

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.