Our Eastern Shore bed and breakfast is the perfect destination for a last-minute vacation or romantic Chesapeake Bay getaway. Located near historic Chestertown, Maryland, we are less than two hours from Washington, DC, Baltimore, MD, and Philadelphia, PA, making Great Oak Manor a convenient spot for your next escape.
Our seasonal specials are designed to help you celebrate Maryland’s Eastern Shore in every season! Surprise a loved one with an unexpected getaway in the middle of winter. Celebrate spring’s return with a much-deserved weekend on the Bay. Discover a multitude of delights while hiking and biking the shore in the summer, or explore country roads amidst the changing colors of fall.
Thanksgiving Dinner
Staying with us over Thanksgiving?
Enjoy a traditional holiday dinner with all of the fixings including turkey 2 ways: Smoked and Cajun Deep Fried
Price: Free for guests who stay 3+ nights and $60 per person for guests who stay 1-2 nights.
*Plus Taxes and Gratuity
Christmas Dinner
Staying with us over Christmas?
Join us for a full Christmas dinner that will leave your hearts warm and bellies full!
Price: Free for guests who stay 3+ nights and $60 per person for guests who stay 1-2 nights.
*Plus Taxes and Gratuity
New Year’s Eve Dinner
Staying with us over New Year’s Eve?
Join us for a sumptuous prime rib dinner with all of the trimmings. Complete with Champagne.
Price: $60 per person for guests. Free for guests who stay 3+ nights.
*Plus Taxes and Gratuity
Romance Package
Planning on celebrating your anniversary at Great Oak Manor?
Let us worry about the special arrangements and have everything waiting for you upon arrival … then you can focus more on celebrating.
- Floral arrangement
- Chocolate Truffles
- Complimentary sparkling wine
Price: $89
Crab Feast
Enjoy fresh steamed crabs in your own private gazebo overlooking the bay. Can be enjoyed indoors if desired.
- One dozen steamed crabs
- Corn on the cob
- Your choice of complimentary beer or wine
Price: $125
A pound of shrimp can be added for an additional fee. Available April through October 31st.
Fall Midweek Special
Book 2 midweek nights (Sunday-Thursday) and get either the 2nd night half off or the 3rd night free through November 15th!*
Book online and use the following promo codes to take advantage of this special!
Half off 2nd night: BOG1/2
3rd night FREE: 3FALL
*Valid for new reservations only, through November 15, 2018.
Active Duty Military
As a small token of gratitude for all that you do, we always offer an additional 10% discount for all active duty military. Simply present your military ID upon check-in and mention this offer upon booking.
Veterans Special
As a special thank you for all that you’ve done, we would like to offer a weekly special. Call to reserve your stay on any Tuesday or Wednesday and receive 20% off your entire stay.
Soup-er Supper
Soup-er Supper
Too cold to venture outside? Enjoy a deliciously warm Soup-er Supper at the manor featuring:
- A bowl of soup, chili or stew (chef’s choice)
- Corn muffins
- Salad
- Slice of pie
- A glass of wine
Price: $20/person plus tax and gratuity
Available November 1st – March 31st
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Cheese Anyone?
Cheese Anyone?
Have a cheese and fruit tray ready and waiting for you in your room, or ask to have it delivered to you just in time to watch the sunset over the Bay.
- Artisan cheeses
- Seasonal fruit
- Crackers
- Fresh lemonade or complimentary bottle of wine
Price: $60
Flower Arrangement
Everyone Loves Flowers
Fresh flowers add a special touch of attention to show your partner or family member that you were thinking of them and just how much you care.
Beautifully arranged flowers, waiting in your room
Price: $50
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