Nestled on the outskirts of Chestertown in Maryland, Great Oak Manor is a magnificent 18th-century country-style estate that overlooks the Chesapeake Bay. Offering a relaxing getaway for travelers, the elegant manor house features beautifully appointed guest rooms with private bathrooms, inviting common rooms for relaxing, mouthwatering breakfasts every morning, and warm and welcoming hospitality. Great Oak Manor offers a range of luxury amenities and guest services, including a complimentary breakfast served every morning, a waterside fire pit for relaxing under the stars, and guests have access to kayaks, canoes, paddleboards, and cruiser bicycles to enjoy. The marina next to the Manor offers a variety of facilities and services to which guests have access, including a swimming pool, a fitness room, a nine-hole golf course and tennis courts. Ideally situated for a relaxing getaway or exploring the quaint streets of historic Chestertown, Great Oak Manor promises an idyllic escape from the city.

10568 Cliff Road, Chestertown, MD 21620-4115, Phone: 410-778-5943

Plan Your Trip

Get Ready to Go!

Need some more help?


Read our Reservations & Travel Planning Tips guide.