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.

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
Picnic on the beach

Let’s Picnic

A delicious picnic meal to enjoy at the Manor or while out adventuring