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.
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 1st.
Blue Crab Chesapeake Charters Sunset Sail Package
Interested in setting sail on the Chesapeake?
Let us know in advance with this package and we’ll have your vouchers all ready for you upon check-in.
- Pre-made reservations for a chartered sail
- 1 ½ hour sail from the Rock Hall Harbor and out onto the Bay (Daily sails or sunset cruise–inquire about specific items)
- Cheese picnic basket with complimentary bottle of wine
Price: $145
Available April through October 1st.
Fall Midweek Special
Book 2 midweek nights (Sunday-Thursday) and get the 3rd free in September and October!*
Book Online and use Promo Code: 3Fall
*Valid for new reservations only, through October 31, 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.
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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Let’s Picnic
Let’s Picnic
Sometimes you arrive and don’t want to go back out for lunch or dinner. This way, you can enjoy a picnic meal on the beach, take it with you kayaking, or have a sunset picnic on the bluff.
- Delicious fresh sandwiches with a choice of Chicken salad, Tuna Salad, Ham or Turkey & Cheese
- Potato Chips
- Homemade sweet snack of the day
- Fresh Fruit
- Iced tea, lemonade or complimentary bottle of wine
Price: $70