Bed and Breakfast in Chestertown, MD

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.

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 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 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).