Great Oak Manor
Escape to Great Oak Manor!

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!

10568 Cliff Road
Chestertown, Maryland 21620
Days Open
DCA Member