Located on Chesapeake Bay in Chestertown, Maryland, the Great Oak Manor is an 18th century country-style bed and breakfast. Experience a blend of relaxation and sophistication as you sit by the water watching the sunset and let your mind roam free at this historical estate.

The Great Oak Manor features cheerily decorated common rooms where you can socialize, read, and enjoy freshly prepared snacks, coffee, or tea. Bicycles and paddleboards are available for use so you can experience the fun and adventure of the Eastern Shore.

Great Oak Manor has 12 inviting suites with elegant touches including plush towels, feather beds, and the finest bath amenities. Each morning you will wake up to a fresh homemade breakfast that you can savor while taking in the stunning bay views.

10568 Cliff Rd, Chestertown, Maryland 21620, 410-778-5943

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