Find a Bed and Breakfast in  Chestertown, Maryland

Chestertown is located on the banks of the Chester River, on the upper eastern shore of Maryland, and it is home to many cozy B\u0026B establishments. In May, Chestertown is the venue for the annual Chestertown Tea Party that commemorates the local merchants' revolt against the British Tea Tax. Chestertown also holds their annual event "Music in the Park," which showcases local and out of area musical talent starting in June and continuing until August. If you are thinking about attending any of these fun family events, why not book a room in advance at a Chestertown bed and breakfast or a Chestertown inn. The Tea Time House Tour is a great way to visist all the historic homes in Chestertown that attract so many visitors. Waterman's Museum is a museum dedicated to the knowledgeable watermen who aided the French in surrounding the British during the American Revolutionary War. Historians will enjoy the Brooks Tavern, home to a rustic atmosphere and delicious food. Those stopping in for a little bit will love the Crossfire Cafe with its easy access from the tree lined streets and delicious deli-style fare.