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Great Oak Manor

Professional Bed and Breakfast hosted by Manager and Innkeeper, Holly McKee

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About The Property

Carefree Elegance on the Chesapeake Bay on Maryland's Eastern Shore, Great Oak Manor is a magnificent Georgian Mansion sitting on the banks of the Bay. The beautiful lawns and landscaping create openness while remaining private. Our B&B has 12 guest rooms and a spacious Carriage House that is perfect for families. Our private beach allows our canoe, kayaks and paddle boards easy access to the water. Take our cruiser bicycles out for a ride on our flat country roads or choose to relax in our Adirondacks by the water or nap in one of the hammocks


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Accepts Gift Cards
ADA Compliant
Breakfast Included
Daily Housekeeping
Fireplace In Room(s)
Free Parking
Free Wi-Fi
In-Room TV(s)
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Manager and Innkeeper, Holly McKee

Holly has been the innkeeper since March, 2017 after being an interim innkeeper with her husband for 4 years prior to that. She loves Great Oak and enjoys the view from her office window of the back lawn and the Bay.

10568 Cliff Road, Chestertown, Maryland 21620