A large brick building with grass in front of a house at Great Oak Manor.A person sitting on a bench next to a body of water at Great Oak Manor.A bedroom with a bed in a room at Great Oak Manor.A group of people sitting at a traffic light at Great Oak Manor.A plate of food on a picnic table at Great Oak Manor.

About The Inn

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. Our evening sunsets are not to be missed!

13 Guest Rooms

Popular Amenities

Accepts Gift Cards
ADA Compliant
Breakfast Included
Daily Housekeeping
Fireplace In Room(s)
Free Parking
Free Wi-Fi
In-Room TV(s)
King Bed(s) On Site
Non Smoking
Pet Friendly
Private Bathroom(s)

About The Innkeepers

Manager and Innkeeper, Holly McKee Innkeeper Photo

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.


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10568 Cliff Road, Chestertown, Maryland 21620