An exceptional experience awaits you at Great Oak Manor. Our 1938 Georgian manor looks out over a picturesque Chesapeake Bay near the historic village of Chestertown along Maryland’s Eastern Shore.

Twelve comfortable accommodations and a delicious breakfast will make you feel right at home. Relax in a hammock shaded by stately walnut trees, recalibrate to nature’s pace as you gaze over an ever-changing bay view. Stroll the expansive lawns or ride further afield in one of our Cruiser Bicycles.

As the new owners of Great Oak Manor our journey in hospitality began over 20 years ago. Today, our focus is on placing the Manor on a trajectory to achieve extraordinary service while creating a deeply personalized experience for our guests. At each touchpoint from website, through arrival, and departure and beyond we aim to build loyal guests and strong relationships, not scale.

We want the Manor to be a place where our guests can focus on the things that matter to them in a place of congenial graciousness. For individual travelers, couples, families, and groups of friends we want to become a first-choice option for connection, for learning, and wellness.

We will be very deliberate in leveraging the rich history of the Manor and the surrounding area to help create the powerful shared experiences from which memories are created.

For many years, Great Oak Manor has delivered a rich hospitality-driven experience to its guests. Under the leadership of General Manager, Brooks Bradbury, we have a bedrock commitment to build on this legacy.




10568 Cliff Rd. Chestertown, MD 21620


(410) 778-5943