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 31st.

Summer Midweek Sale

Book a midweek stay (Sunday-Thursday) in a 1st or 2nd-floor room in the Carriage House this June 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.

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.

Private Dinner for Two

Private Dinner for Two

Enjoy a very special evening with your one and only without having to leave the property!
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
60 Minute Massage at Great Oak Manor

60 Minute Massage

Rejuvenate with a refreshing 60 minute massage
Reiki Session at Great Oak Manor

Reiki Session

Experience the ancient healing practice of Reiki (Rei "guided" Ki "life force energy")
Reflexology Foot Massage at Great Oak Manor

Reflexology Session

Promote self-healing with our specialized 1 hour Reflexology Session