Hotels in Chestertown, MD

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.

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 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 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.