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.

Thanksgiving Dinner

Staying with us over Thanksgiving?

Enjoy a traditional holiday dinner with all of the fixings including turkey 2 ways: Smoked and Cajun Deep Fried

Price: Free for guests who stay 3+ nights and $60 per person for guests who stay 1-2 nights.


*Plus Taxes and Gratuity

Christmas Dinner

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

New Year’s Eve Dinner

Staying with us over New Year’s Eve?

Join us for a sumptuous prime rib dinner with all of the trimmings. Complete with Champagne.

Price: $60 per person for guests.  Free for guests who stay 3+ nights.


*Plus Taxes and Gratuity

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 31st.

Fall Midweek Special

Book 2 midweek nights (Sunday-Thursday) and get either the 2nd night half off or the 3rd night free through November 15th!*

Book online and use the following promo codes to take advantage of this special!

Half off 2nd night: BOG1/2

3rd night FREE: 3FALL

*Valid for new reservations only, through November 15, 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.

Roasted Tomato Soup

Soup-er Supper

Too cold to venture outside? Enjoy a deliciously warm Soup-er Supper at the manor.
Fruit and cheese plate

Cheese Anyone?

A cheese and fruit tray ready in your room
Bouquet of flowers

Flower Arrangement

Beautifully arranged flowers waiting in your room