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Great Oak Manor Inn
Chestertown, Maryland

Great Oak Manor, located near historic Chestertown and Rock Hall, on the Eastern Shore, is acclaimed in Country Inns Magazine as "that regal 25 room mansion resting on the gentle banks of the Chesapeake Bay...".

Come for a getaway to Great Oak where the only honking comes from the geese, where the closest highway is the geese flyway and where the only traffic you see from your room are the boaters sailing the crystal water just 200 yards away.

Great Oak Manor offers a private and secluded setting on the Chesapeake Bay for that "get-a-way from it all" feeling in a magnificent 1700's style country estate with 11 guest rooms. And when you want to explore you will find Chestertown, Rock Hall and the Eastern Neck Refuge close by.

Featured on the Today Show , July 2005 with Peter Greenberg

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Each of the 12 guest rooms has a private bath, five have working fireplaces, seven have Bay views, all have phones and all are air-conditioned.

Click Here to Check on Room Availability

The Inn features an expansive terrace offering exquisite views of the bay. Lounge chairs are provided for those who wish to cozy up with a book or to just sit and watch the sunset.

Full breakfast with our compliments.

Afternoon refreshments served in the chesapeake room.

Guest Information

  • Rates: $159 to $599 depending on season
  • Eleven guest rooms located on the Chesapeake Bay, individually heated & air conditioned for your comfort, five with working fireplaces, seven with water views.
  • Gardenview Handicapped accessable suite on first floor All with phones, safes, irons/boards, TV, hairdryers, luxurious plush bathrobes, and abundant amenities.
  • Smoking not permitted in guest rooms, only in designated smoking areas.
  • All rooms have a private bath & king size bed with feather toppers.
  • Private beach and gazebo with comfortable bay rockers and adirondacks for sunset watching.
  • Historic Chestertown, Washington College, and Eastern Point Nature refuge within ten minutes.
  • Varied and superb dining options closeby.
  • We are limited Pet Friendly, we do take Children over the age 12,( Children of all ages welcome with whole house gathering, i.e. Family reunions, weddings)
  • Complimentary bicycles and lawn games for our guests.
  • Yachting and fishing available, weather and seasons permitting.
  • Two night minimum on stays over Saturday during high season (April through November).
    Check-in time 3:00 P.M. to 8:00 P.M.
    Check-out time - before noon.

Whether it's antiquing or shopping in Chestertown or Rock Hall, or dining at one of our many fine restaurants, there's much to do within minutes of the Inn.   On any day there's fishing, sailing, canoeing, kayaking, taking a shot at sporting clays, or cycling across the County along scenic byways. Next door at the landing is golfing, tennis, and birding... or just relax and watch the sunset from the Inn's own terrace.

Great Oak Manor offers complete conference and meeting facilities,
privacy, seclusion and the convenience of first-class accommodation on Maryland's Upper Eastern Shore.

As featured in Chesapeake Life's 1999 Winter edition "Great Gatsby on the Chesapeake".
Recognized by American Historic Inns as one of their "Top Ten Most Romantic Inns" for 2000.
Approved by Maryland Bed and Breakfast Association.

Gift certificates available.

Great Oak Manor - a year round destination. A step off the fast track to a place where the ambiance of elegant living has been preserved

Great Oak Manor Bed & Breakfast on the Chesapeake Bay is a member of the following associations:
The Select Registry- Distinguished Inns of North America,
Maryland Bed and Breakfast Association,
Professional Association of Innkeepers International (PAII)
Kent County Lodging Association

Great Oak Manor Inn
10568 Cliff Road
Chestertown, Maryland 21620
(410) 778-5943
(800) 504-3098

Fax: (410) 810-2517
Email: info@greatoakmd.com
Homepage: www.greatoakmd.com
Innkeepers: Buddy Reed and Mike Kuhn

  Hits Since 2/07/05

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