Best apartment offers in Chestertown, MD

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 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 three-bedroom apartment is located just 0.8 km from the bay in Rock Hall, a quiet location close to Rock Hall Harbour and Rolphs Wharf Marina. The apartment has received excellent ratings from previous guests.
This spacious property can accommodate up to eight guests and features a well-equipped kitchen, a terrace, a garden, and parking for three vehicles. Enjoy the peace and quiet of the location while having easy access to the bay for boating, paddle boarding, kayaking, birdwatching, and cycling.

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 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.

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 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 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 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 five-bedroom guesthouse in Worton, a short drive from Betterton Beach, offers convenient access to the Kent Museum and Historical Society of Kent County Maryland and Hidden Lake.
The 139 square metre (approximately 1496 square feet) property sleeps ten guests and includes a full kitchen, microwave, fridge, two bathrooms, air conditioning, parking, and Wi-Fi; hunting and birdwatching opportunities are also nearby.

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 waterfront property is situated just 14.5 kilometres from Washington College, River Arts Chestertown, and Rolphs Wharf Marina, offering easy access to local attractions and a peaceful setting. The home has received excellent ratings for cleanliness, location, and user experience, making it a popular choice for travellers.
The house spans 139 square metres and comfortably accommodates up to six guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a terrace, a garden, a spa, a bar, parking, and free breakfast, 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.