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.