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Chestertown, Maryland (MD) Bed and Breakfast: Only one and one half hours drive from Washington D.C., Baltimore and Philadelphia, the Manor is listed as one of Maryland's historically significant homes. Great Oak Manor, a year round destination for get-aways and Maryland corporate events, is 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


Chestertown, Maryland

A palatial 1700's style Georgian Manor set on 12 acres overlooking the Chesapeake Bay on Maryland's Eastern Shore!
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Introduction

Please see our Valentine's Specials!

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, a Chesapeake Bay Maryland bed and breakfast where the only honking comes from the geese, where the closest highway is the duck flyway, and where the only traffic you see from your room are the boaters sailing the crystal water of the Chesapeake Bay Waterfront, just 200 yards away.

Great Oak Manor 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 twelve guest rooms. Each guest room of our Chesapeake Bay Bed and Breakfast is unique from the grand Marmaduke Chesapeake Bay waterside room at the top of the spiral staircase to quaint sloped ceiling rooms on the third floor.

Each room is individually air conditioned and has its own story to tell. All rooms have a private bath, king size bed with feather toppers (one room with four-posted Queen), phones, safes, irons/boards, TV, hair dryers, luxurious plush bathrobes, and abundant amenities. Seven rooms have water views, five have working fireplaces, and one room has an electric fireplace.

Sitting with views of the bay, the elegant fireplace dining room features a full breakfast with Manor-baked muffins, hot entree, cereals, yogurts, and always fresh fruit. Afternoon refreshments are served in the Chesapeake Room, and evening port and sherry are served in the music room.

The Bed and Breakfast Inn features an expansive terrace offering exquisite views of the Chesapeake Bay. Lounge chairs are provided for those who wish to cozy up with a book or to just sit and watch the sunset. Our private and tranquil beach offers guests a peaceful retreat from a hectic world. Guests can relax and enjoy the grounds, venture out on the Inn's ten speed bikes, swim off the private beach, and enjoy complimentary golf, swimming, and tennis at the Great Oak Yacht Club next door.

View from the Lawn

Special Packages

Rent the Entire Inn
Rent our entire Inn with 11 bedrooms for your family or business group.....(more)

Romantic Winter Dinner Weekends
Champagne, flowers, evening turndown, massages, live jazz, hors d' oeuvres, five course dinner with five wines and more....(more)

Active Military Personnel Discount
10% room rate discount to all active Military Personnel....(more)

Romance and Relaxation Getaway
A romantic get a way where relaxation is guaranteed with a massage in your room for each of you. ....(more)

Winter Special
Mid Week Winter Special, Stay one night get the second night half price in our Mid price rooms....(more)

Dinner at the Inn
Join us for a romantic weekend!....(more)

Business Corporate Conferences
Plan your next meeting retreat on the shores of the Chesapeake Bay in Maryland. We are located two hours away from major....(more)

Wedding Anniversary Package
Voted one of the Top 10 Romantic Inns....(more)

As featured on The Today Show with travel editor Peter Greenberg, July 2005,
and also featured in the February 2004 issue of Southern Living Magazine;
in The Washingtonian "Dream Weekends", April 2003 & in Baltimore Magazine July 2003 "Bay Watch";
in Chesapeake Life June 2003 issue & in Chesapeake Life 1999 winter edition "Great Gatsby on the Chesapeake"
Recognized by American Historic Inns as one of their "Top Ten Most Romantic Inns" for 2000.

Select Registry

1.5 hour diving time from Washington DC, Baltimore, and Philadelphia!

Great Oak Manor Bed & Breakfast on the Chesapeake Bay is a member of the following associations:
   The Maryland Bed & Breakfast Association
   Select Registry, Distinguished Inns of North America

  Click-on these pages for more information:

 | Guest Rooms/Rates | History | Special Packages | 2008/2009 Room Rates | Reservation Request Form |

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Great Oak Manor Bed & Breakfast on the Chesapeake Bay
 10568 Cliff Road
Chestertown, Maryland   21620
 (410) 778-5943
(800) 504-3098
Fax: (410) 810-2517
email:

Visit our web site at:
www.greatoak.com

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since June 16, 1997

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