Chestertown, Maryland 21620

Share in a Part of History

Great Oak Manor announces The Great Oak Manor Club nestled within the lush surroundings of twelve acres overlooking the Chesapeake Bay on the Eastern Shore of Maryland.

Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside twelve hundred feet of Chesapeake Bay waterfront. The Chesapeake Bay is aglow in warm sunsets, towering Oaks gently kiss the skyline, and you can let your body rest as your mind wanders. Great Oak Manor Club offers the finest in luxury, where all of your whims are cared for, day and night. Great Oak Manor Club possesses grace and elegance that is tempered with a sense of days gone by. From the moment you reach the meandering roads of the Eastern Shore, you feel as if you are traveling back through time.

Great Oak Manor Club will provide more than a place to sleep. We offer a place to dream and rest amongst the memories of guests from the past. Relax in the history and intimacy of the Manor while enjoying the benefits and amenities of membership. Great Oak Manor Club Members will share a piece of history with Frank Russell and the D’Oench family. So if you have been considering a vacation home but hesitate to make that huge investment for what may amount to only a few weeks of usage per year? Great Oak Manor Club can offer you a lifestyle for those weeks that is unparalleled and gracious beyond what could be experienced in an expensive under used vacation home.