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Escape to Great Oak Manor

Come to our quaint bed and breakfast on Maryland’s Eastern Shore, where the Chesapeake Bay is aglow in vibrant, warm sunsets; where towering oaks gently kiss the skyline; and where you can let your body rest and your mind wander.

Tucked away on the outskirts of Chestertown, Maryland, our magnificent 18th century country-style estate rests alongside the waterfront. With 12 guestrooms and various common rooms, Great Oak Manor offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night.

Whether you’re adventurous, need to get away, or just want to be taken care of, there’s something here for everyone. Spend an afternoon perusing the quaint streets of historic Chestertown, exploring the Eastern Neck Refuge, sampling the fresh catch in Rock Hall, or just curl up in the arms of a weathered Adirondack chair to soak up the view.

Aside from offering a relaxing getaway for travelers, Great Oak Manor also serves as the ideal location for various events, retreats, parties, and weddings. Welcome to our home, stay a while.