Places to stay in Chestertown, MD

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 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 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 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 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 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 four-bedroom house is situated in a peaceful residential area, approximately 77 kilometres from New Castle Airport. The property offers a spacious 300 square metre layout, accommodating up to 27 guests and featuring amenities such as a swimming pool, garden, and private parking.

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 Chestertown townhouse, located on a quiet street in the historic downtown area, is steps from the farmers' market, Chester River, and numerous restaurants.
The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with dishwasher, a private patio for al fresco dining, and free on-site parking; enjoy easy access to local festivals and waterfront walks.

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 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 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 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 carriage house is situated on a peaceful historic farm, just 3 kilometres outside of Chestertown. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The property features two bedrooms and one bathroom, comfortably accommodating up to five guests. The house is fully equipped with a fridge, freezer, microwave oven, dishwasher, and air conditioning, and guests can enjoy a private garden and parking.

This cottage is located in Chestertown, within 1.5 kilometres of Washington College, River Arts Chestertown, Garfield Center for the Arts, Sumner Hall, and the Chestertown Historic District.
This property offers a well-equipped kitchen with a microwave and dishwasher, air conditioning, and on-site barbecue grills, with WiFi available in public areas.