Search accommodations in Chestertown, MD

This luxury estate, located in Worton, Maryland, is situated on a river with views of the bay, offering proximity to the Betterton Historic District and the Chesapeake Bay, approximately 8 kilometres away.
This expansive 14,400 sq ft residence on a 90-acre private estate accommodates up to 25 guests with 8 bedrooms and 6 bathrooms, featuring resort-style amenities including a swimming pool, jacuzzi, and a gourmet kitchen ideal for large gatherings.

This waterfront home is situated just a short distance from Chestertown’s historic district, offering easy access to cultural attractions and the beautiful Chesapeake Bay. The property has received excellent reviews from previous guests, highlighting its tranquil location and comfortable amenities.
This spacious three-bedroom property can comfortably accommodate up to 10 guests. Amenities include a fully equipped kitchen, a private dock, kayaks, bikes, a hot tub, and a tennis court, providing everything you need for a relaxing and enjoyable stay.

This Fairlee apartment is conveniently located just a short distance from Great Oak Manor and Great Oak Landing Marina, offering easy access to a range of attractions and amenities. The apartment has consistently received excellent ratings for cleanliness, location, and overall user experience.
The property features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. The apartment includes a fully equipped kitchen, air conditioning, a garden, parking, and internet access, ensuring a comfortable and enjoyable stay.

This Chestertown property, a two-bedroom, two-bathroom flat, is located near historic streets and the Chester River, offering convenient access to downtown attractions, including art galleries, and Wilmer Park, all within 1 kilometre of the accommodation.
This pet-friendly apartment accommodates up to six guests and features a well-equipped kitchen with a Cuisinart dual coffee maker, air conditioning, a fireplace, a fenced garden with a furnished deck, and off-street parking.

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 Chestertown apartment is located on the second floor of a historic building on the main street, just a short walk from shops, restaurants, and the waterfront. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment is spacious and can accommodate up to four guests. It is equipped with a fully fitted kitchen, a washing machine and dryer, and a Smart TV, as well as high-speed Wi-Fi and off-street parking for one car.

This charming Victorian house is situated in Chestertown, just a short walk from the historic district and waterfront, providing easy access to the town's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious home offers four bedrooms and two and a half bathrooms, making it ideal for families or groups. Guests can enjoy a gourmet kitchen, a private garden, and a garage with electric vehicle charging, perfect for exploring the area.

This riverfront property is situated just three miles from the centre of Chestertown, a charming town with a rich history and a bustling waterfront, and is also within easy reach of other popular destinations such as Rock Hall, Annapolis and St. Michaels. The property has received excellent ratings for its location, cleanliness and overall experience.
The house has three bedrooms and can accommodate up to ten guests, making it ideal for families or groups of friends. Guests can enjoy a range of amenities including a fully equipped kitchen, a private dock and boat lift, a spacious terrace, a garden, a fitness centre and air conditioning.

This charming 3-bedroom apartment is situated in the historic district of Chestertown, just a short walk from the bustling High Street and two blocks from the picturesque Chester River. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers ample space for families or groups of friends, with three bathrooms and a capacity of six guests. Enjoy modern amenities such as a fully equipped kitchen, a washer and dryer, a gas fireplace, and a private garden with a screened porch and a brick terrace, perfect for relaxing evenings.

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.

Owl Cottage is a renovated carriage house located in the centre of Chestertown, just a short walk from the historic district and waterfront. This charming cottage offers a unique blend of historic charm and modern convenience.
The property has a unique layout with a ground floor bedroom, a second floor living/kitchen area with a bathroom, and a third floor loft with a queen-sized bed. The cottage comfortably sleeps up to four guests and includes a private garden, patio, and pet-friendly amenities.

This six-bedroom, five-bathroom waterfront property in Chestertown is situated on the Chester River, a short 0.4-kilometre walk from the historic town centre.
The 14-guest dwelling boasts two kitchens, a ground-floor great room with a pool table and 75-inch television, extensive outdoor space including a private pier with kayaks and paddleboard access, and fresh 2021 updates.