Great Oak Manor offers guests vacation and getaway lodging on the Eastern Shore of Maryland on the outskirts of historic Chestertown. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, we are a 90-minute drive from Philadelphia, less than two hours from each of Washington, D.C. and Baltimore and a 3-hour drive from New York City.

Our preferred limousine company is Prince Limousine (410-778-4860), a company that can pick up individuals and groups from Philadelphia International, Washington Reagan, Washington Dulles, and Baltimore-Washington Airports. The closest Amtrak station is in Wilmington, DE, 1-hour from the Manor.

We would be happy to assist you with your ground transportation needs.


Please enter our actual address into your GPS. It is 10568 Cliff Road, Chestertown, Maryland 21620.

  1. Follow the directions to Handy Point Road.
  2. Note that once you are on Handy Point Road, proceed 1.8 miles and then veer left onto Great Oak Landing Road. DO NOT TURN RIGHT INTO TILDEN LANE.
  3. Stay left at the fork in the road shortly after Tilden Lane.
  4. Drive past the farm silos and through the 1st set of red brick pillars.
  5. Continue straight past the golf course on your left.
  6. Continue straight until you see the Great Oak Manor sign on your left. Turn left onto the Manor driveway and then through the red brick pillars to the large red brick manor house.