Chestertown is home to 300 years of history, so be ready to experience colonial life on your next bed and breakfast visit! With a mix of history, shopping, arts, and exceptional dining, Chestertown is perfect for families, couples, and business travelers looking for relaxation and convenience. When you arrive at your bed and breakfast, your helpful bed and... » show more breakfast innkeepers will be happy to tell you about Chestertown’s rich history, dating back to colonial times. With rich traditions that go back hundreds of years, bed and breakfast guests are sure to appreciate the past when vacationing in Chestertown. Take a stroll and enjoy the colonial homes near your bed and breakfast, or explore the Saturday Farmers Market. Be sure to explore the shopping of Chestertown, where store fronts are filled with one-of-a-kind items, and fresh flowers line the historical streets. Bed and breakfasts guests can take in some local culture at one of the dozen galleries, studios and shops in Chestertown featuring local, regional and international artists. Ask your bed and breakfast innkeepers to recommend their favorite local eatery, and feast on delicious food, from the Bluebird Tavern to the Village Bakery and Cafe. Your bed and breakfast home away from home in Chestertown is waiting! Discover the perfect bed and breakfast today and begin planning your Chestertown getaway! « show less