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!

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
  • Bottle of wine

Price: $99

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 a six-pack of beer or wine

Price: $145

A pound of shrimp can be added for an additional fee. Available April through October 31st.

Golf Package

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.

Fall Midweek Special

Book 3 midweek nights (Sunday-Thursday) and get the 3rd night free!

Promo code: 3Fall

*Valid for new reservations only, through October 31, 2019. Valid for all rooms except Hynson, Ringgold, and Conservatory.

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.

Red wine being poured into a glass

Red Wines

Up the romance with red wine from an award-winning local vineyard.
Glass of white wine in a vineyard

White Wines

Enjoy a bottle of locally-sourced, award-winning white wine.
roasting s'mores

S’mores Kit for 2

We provide the ingredients and the fire, you provide your cooking skills.
Private Dinner for Two

Private Dinner for Two

Enjoy a very special evening without having to leave the property!
Fruit and cheese plate

Cheese Anyone?

A cheese and fruit tray and a bottle of wine 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
Reflexology Foot Massage at Great Oak Manor

Reflexology Session

Promote self-healing with our specialized 1 hour Reflexology Session