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.
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.
Summer Midweek Sale
Book a midweek stay (Sunday-Thursday) in a 1st or 2nd-floor room in the Carriage House this June and get up to $300 off your entire stay!*
Book 2 midweek nights (Sunday-Thursday) and get $100 off your stay! PROMO CODE: SUMMERFUN2
Book 3 midweek nights, and get $200 off your stay!! PROMO CODE: SUMMERFUN3
Book 4 midweek nights, and get $300 off your stay!!! PROMO CODE: SUMMERFUN4
*Valid for new reservations only.
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.