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.
Girls’ Getaway Package
Get a group of friends together for a relaxing stay in our Carriage House, with majestic views of Chesapeake Bay and room for 4 to 6 people. Book two or more nights, and enjoy all of the following during your stay:
- Bottle of sparkling wine (for mimosas – orange juice included)
- Cooking class with a meal
- Wine tasting at Crow Vineyards and Winery
- Stocked fridge for in house breakfast
- We keep the woodbox stocked with firewood
Price: $99 per person plus room rate
Start your happily ever after at our romantic Maryland bed and breakfast. Enjoy your stay with the following special details:
- Two soft and luxurious Great Oak Manor bathrobes
- Two exclusive pottery mugs to take home with you
- A scrumptious breakfast served to you in-room, complete with Champagne
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
- Bottle of 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 a six-pack of beer or wine
A pound of shrimp can be added for an additional fee. Available April through October 31st.
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.
Cozy Mid-Week Winter Special
What is more romantic than a cozy winter stay in Chesapeake Bay? Grab your loved one and save big this holiday season with our mid-week special. For every night you stay, get a percentage off your room starting with 10% off the first night, 25% off the second night, 33% off the third night of your stay. Use promo codes: MidweekWinter-1; MidweekWinter-2; MidweekWinter-3
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.