Maryland Bed and Breakfast | Romantic Luxury Inn | Waterfront Bed and Breakfast

Awaken to the sounds of nature, wander down the Grand Staircase to the Waterfront and sit by the Chesapeake Bay.

Stroll into the Dining Room for a warm country breakfast, then take a walk in the Country.

Visit Historic Chestertown, listen to the quiet of small town America.

Return to Great Oak Manor, dine in the area's many fine restaurants and join us for Port and Sherry in the evening as we watch the panoramic sunset over the Bay.

Escape to Great Oak Manor, a quaint Maryland bed and breakfast on the eastern shore, where the Chesapeake Bay is aglow in 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 11 guestrooms, Great Oak offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night.

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.

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