Search accommodations in Chestertown, MD

This 19th-century retreat, located in Still Pond, offers an apartment just a 15-minute drive from historic Chestertown and is conveniently situated near Rock Hall, Betterton Beach, Georgetown, and local vineyards.
This 42 square meter apartment accommodates up to three guests, featuring a private living room with a pullout sofa, a queen bedroom with a Purple mattress, an en-suite bathroom with a multi-head shower, and an in-suite kitchenette, with shared access to a wraparound porch and farmhouse deck ideal for boaters.

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.

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 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 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 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 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 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, located in the historic district, offers a riverfront position on the Chester River, within easy walking distance of the town's attractions.
The third-floor flat boasts a king-size bed, a well-equipped kitchen including a four-burner range and oven, a private rooftop deck with Chester River views, and complimentary access to kayaks/canoes, accommodating up to two guests.

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.

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.

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.