Great Oak Manor provides more than a place to sleep. Located on the Chesapeake Bay, we offer a place to dream. Make yourself comfortable as you take a look at each one of our guest rooms in this Chestertown, Maryland luxury waterfront inn. Rest amongst the softest sheets on comfortable beds topped with down featherbeds. A luxury  robe awaits your arrival—as well as bottled sparkling water, a light snack, and the finest bath and shower amenities .