This Georgian Style Chestertown, MD Bed and Breakfast is situated on the Chesapeake Bay on Maryland’s Eastern Shore. The 12,000-square-foot estate has everything you need for the perfect getaway. Enjoy luxurious accomdations in any of our 13 guest rooms, featuring cozy fireplaces, inviting skylights, large clawfoot tubs, and modern amenitites. Spend the day exploring the sprawling grounds or private waterfront. Enjoy laying in the hammock, bird watching, and dining for breakfast with views of the Bay. Looking for something fun to do? Bike over to Chestertown and explore its rich history. Great Oak Manor is conveniently accessible from Washington D.C., Baltimore and Philadelphia – all within a comfortable 1-1/2 hour driving distance. Whether it’s antiquing or shopping in Chestertown or Rock Hall, or dining at one of our many fine restaurants, there’s much to do within minutes of the inn. On any day there’s fishing, sailing, canoeing, kayaking, taking a shot at sporting clays, or cycling across the county along scenic byways. Next door at the landing you’ll find golfing, and tennis….or relax and watch the sunset from the Inn’s own terrace. Great Oak is the place to come home to!
Great Oak Manor
10568 Cliff Rd
Chestertown, MD 21620
Host(s): Richard and Holly McKee