About

Great Oak Manor is a newly renovated 12-room luxury boutique hotel, plus Carriage House, situated on 15.2 private acres with a Grand Lawn and private beach along Chesapeake Bay in bucolic and historic Kent Country on Maryland's Eastern Shore eight miles from Chestertown, MD, with cobblestone streets lined with trees and gas-lit lanterns, beautiful Colonial, 18th- and 19th-century homes along with shops, galleries and restaurants that exudes an elegant small-town Southern charm. 

This Georgian-style manor was originally designed in 1938 by the Maryland architect Douglas Gorden Braik and was styled after an 18th-century English country retreat.  In the late 1940s - 50s, Great Oak Manor was owned by a self-made businessman, Frank Russell, who ran his shore home an exclusive premier club and (at the time illegal) casino, hosting celebrities such as President John F. Kennedy, American broadcaster & entertainer Arthur Godfrey, writer Ernest Hemmingway and actor Robert Mitchum. 

Today this is 12,000 sq ft. manor, located on an oasis of stately trees, expansive lawns and ever-changing picturesque Chesapeake Bay views, is newly owned by a private family as of 2022 and in 2024 completed a full renovation of the first-floor common areas and guest rooms.

Great Oak Manor is a gracious property to host family gatherings, couples or group friends’ getaways, celebrations from milestone birthdays and anniversaries to graduations, or intimate/micro-weddings.