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.
Summer Golf Package
Perfect for dad! Experience the #1 rated golf course in Delaware!
Back Creek Golf Course is a 45-minute drive away from our Manor and we’re excited to offer our guests great golfing packages this season:
$100/person on weekdays (Monday – Friday)
$125/person on weekends (Saturday – Sunday) and Federal Holidays
Packages include golf cart, rental clubs, lunch, a draft beer or fountain soda.
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 summer 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, through August 30, 2019.
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.