Luxurious Eastern Shore Waterfront Lodging on the Chesapeake Bay

Great Oak Manor has 12 rooms for your manor stay featuring their own unique decor with individual highlights such as a cozy fireplace, a spacious bath with skylight, inviting French doors leading to the garden, or a rich red bathroom. Check out each room for their individual styles and rates.

Find out more about our reservation policies.

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Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay in Chestertown, Maryland, we offer a place to dream. Make yourself comfortable as you take a look at each one of our guest rooms. Rest amongst the softest sheets on comfortable beds. A luxury robe awaits your arrival—as well as bottled water, a light snack, and the finest bath and shower amenities.

At Great Oak Manor, we understand how difficult it is to leave your furry family members at home or in the kennel. For your getaway on the Eastern Shore, we welcome you to bring along your pets. We have three designated pet-friendly rooms: the Sterling, Roese and the Caulk Suites. Both rooms have either direct or close access to the outdoors. Let us know upon reserving if you intend to bring your pet with you as we do have pet fee of $25.

Every morning is not only met with stunning views of the Chesapeake Bay, but also a full breakfast with seasonal fresh fruit, homemade baked goods, cold cereal, and a hot entrée, such as French toast, quiches, or egg strata. Enjoy your breakfast in the dining room, or take it out to the terrace for a better view along the Eastern Shore.

*Please note that all rooms have a 2 night minimum for weekend stays. We will release this policy on the Wednesday prior to the weekend. The rates above show a range that includes in/off season and weekday/end rates.