There is a special place just waiting for you on the Chesapeake Bay on Maryland’s Eastern Shore. Our Chestertown, Maryland bed and breakfast is a magnificent country estate built in the Georgian Style. It is a charming B&B with twelve guest rooms and a fabulous family style accommodation in addition to spacious common areas.

Whether you want to be active or simply relax, the options are plentiful. Take a bicycle ride on safe country roads, or explore the water from our private beach by kayak, paddle board, or canoe. Walk from our beach to the marina next door where you have access to a swimming pool, a fitness center, and a nine-hole golf course. To slow down, relax in a hammock shaded by stately old walnut trees, sit by the bay in an Adirondack chair or stroll the expansive lawn. Be sure not to miss our spectacular sunsets!

Select Registry
2018 Certificate of Excellence from TripAdvisor
Diamond Collection BedandBreakfast.com Member

COVID-19 Travel Information

We’re working hard to keep our guests healthy and safe, and are continuing to monitor the Coronavirus situation. Please click below for the latest updates. We are here for you!

Learn More