Great Oak Manor is a luxury boutique hotel set in a 1938 Georgian manor overlooking the Chesapeake Bay on Maryland’s Eastern Shore. The property offers a peaceful setting for guests seeking relaxation, connection, learning, and wellness, with attentive service and views of the bay. Its accommodations include 12 individually decorated rooms and suites, along with an expansive Carriage House Suite, featuring comfortable beds and luxurious amenities.

The manor also offers farm-to-table culinary experiences prepared by its executive chef with ingredients from the property’s garden and regional farmers and purveyors. Through its Taste of Great Oak series, guests can enjoy weekend culinary events featuring guest chefs and distinctive cuisine. Great Oak Manor hosts corporate retreats, family gatherings, friends’ weekends, and intimate weddings, and provides spaces for groups to come together. Guests can also enjoy the grounds, a small beach, a fire pit, biking, and yoga. Located near Chestertown, the manor invites visitors to book a stay and experience the Chesapeake Bay at a more relaxed pace.