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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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Special Packages

Specials!

Rent the Entire Inn
Our 25 room estate is the perfect setting for family reunions or business retreats. We sleep 24 guests, double occupancy ,with private baths. Full breakfast will be served daily and all of your dinners can be caterered and served in our lovely dining room.
With all of the common rooms we offer you are sure to have plenty of space to have fun or unwind after a days meeting.
You may contact John to discuss all the details to make this a remarkable vacation.

Romantic Winter Dinner Weekends

Friday Evening
Champagne and Flowers in Suite
Evening Turndown
Massages Optional - $75 (per person - one hour)

Saturday Evening
Casual Elegance of Dress
Live Jazz and Classical in the Music Room with Stefan Scaggiari
Butler Served hors D'oeuvre and Wine
Five Courses, Four Wines

Chef Rob Jester - Culinary Institute of America
Host and Hostess - Cassandra and John Fedas

Platinum Rooms $788 double Occupancy
Gold Rooms $688 double Occupancy (some with water views)
Silver Rooms $598 Double Occupancy

(We recommend that you reserve early!)

Active Military Personnel Discount
10% Room Rate Discount to All Active Military Personnel.
A big thanks from all of us for your bravery and for your sacrifices.

Romance and Relaxation Getaway (8/2/2008 thru 10/31/2008)
Enjoy a relaxing two night stay with Complimentary Champagne or Wine
Two Massages en Suite
Platinum Rooms with waterfront views of the Chesapeake Bay and fireplaces are available for $800 Friday and Saturday nights or $695 Sunday thru Thursday. Enjoy a wonderful breakfast on our beautiful garden patio overlooking the Bay.

Winter Special (12/1/2008 thru 3/28/2009)
Mid Week Winter Special. Come enjoy the beauty of the Eastern Shore in Kent County. Stay one night and get the second night half off in any of our lovely mid range rooms. Many have fireplaces with beautiful views of the 12 acre Estate, others have water views of the Chesapeake Bay. Our Library has over 500 volumes of books to curl up with in front of our fireplaces. You may walk our private beach or play a round of golf next door. Or you may choose to explore the charming town of Chestertown, filled with historic homes, art galleries, and wonderful restaurants

Dinner at the Inn (12/2/2008 thru 3/30/2009)
Arrive to champagne split and a rose or seasonal flowers.
Chocolates by the bed and turn down service provided.
Optional massage $75.00 per hour per person.

SATURDAY Wine Pairing Dinner Chef Rob Jester, Culinary Institute of America

  • Wine cocktails
  • Butler served hors-d?oeuvres and live jazz
  • Five courses
  • Four paired wines

    Platinum - $788 / Gold - $688 / Silver - $598

    Two nights over Saturday, check in 3pm;
    Rates are for double occupancy, two dinners, plus tax. We will have this special throughout the winter months. Please check our web site for next available date

    Business Corporate Conferences
    Plan your next business retreat at Great oak Manor. We have a beautiful conference room overlooking the Chesapeake Bay. We seat from 12 up to 60. Our Inn has many lovely common rooms for break out meeting. We can accommadate 24 guests with double occupancy, and have other accomadations nearby if needed. Contact John Fedas to make arrangements for your group. All off your meals can be provided in house.

    Wedding Anniversary Package
    Great Oak Manor Inn, is the perfect estate setting for a relaxing getaway or a weekend of romance. The Manor will meet your every need, with 1200 feet of waterfront on the Chesapeake Bay, and the most beautiful sunsets on the eastern Shore of Maryland.
    Arrive to a split of complimentary Champagne, or we would be happy to make arrangements to have a full bottle of your choosing. Flowers can be waiting your arrival. We have a wonderful massage therapist that will come to your room to massage you for one hour or 90 minutes. Arrangements will need to be made in advance

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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

    You were visitor number to
    http://www.bbonline.com/md/greatoak/
    since June 16, 1997

    Maryland Bed and Breakfasts | Chestertown Bed and Breakfasts
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