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.
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
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
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
A pound of shrimp can be added for an additional fee. Available April through October 31st.
Book 2 midweek nights (Sunday-Thursday) and get either the 2nd night half off or the 3rd night free through December!*
Book online and use the following promo codes to take advantage of this special!
Half off 2nd night: BOG1/2
3rd night FREE: B2GO
*Valid for new reservations only. Excludes November 22, December 24, 25, 30, 31.
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.
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.