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.
Romantic Fireside Dinner for Two
Enjoy a romantic private dinner by the fire throughout the month of February. Hurry and reserve your spot now as we can only accommodate one per night!
Sample Menu:
- Small Appetizer Bite
- Fresh Greens & Citrus Salad
- Choice of Entree: Petite Filet or Salmon en Croute
- Choice of 2 Sides: Duchess Potatoes, Quinoa & Wild Rice, Roasted Asparagus, or Green Beans Almondine
- Choice of Dessert: Salted Dark Chocolate Pots de Crème or Homemade Ice Cream
Price: $75/person
Call (410) 778-5943 now to Reserve!
*Available until March 31st.
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.
Valentine’s Special
Join us in February and make every day Valentine’s Day! Book any stay in February and add a bottle of sparkling wine & a box of handmade chocolate truffles for just $35!
Just choose your Valentine’s getaway dates, find your favorite room, and add this to your reservation when you book online.
Romantic Fireside Dinner for Two
Enjoy a romantic private dinner by the fire throughout the month of February. Hurry and reserve your spot now as we can only accommodate one per night!
Sample Menu:
- Small Appetizer Bite
- Fresh Greens & Citrus Salad
- Choice of Entree: Petite Filet or Salmon en Croute
- Choice of 2 Sides: Duchess Potatoes, Quinoa & Wild Rice, Roasted Asparagus, or Green Beans Almondine
- Choice of Dessert: Salted Dark Chocolate Pots de Crème or Homemade Ice Cream
Price: $75/person
Call (410) 778-5943 now to Reserve!
*Available until March 31st.
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!
We’ll customize a menu based on your preferences that will include a fresh salad, entrée with two sides, and a dessert.
Price: $100/couple plus tax and gratuity
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Soup-er Supper
Soup-er Supper
Too cold to venture outside? Enjoy a deliciously warm Soup-er Supper at the manor featuring:
- A bowl of soup, chili or stew (chef’s choice)
- Corn muffins
- Dessert
- A glass of wine
Price: $20/person plus tax and gratuity
Available November 1st – March 31st
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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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Reiki Session
1 Hour Reiki Session
Experience the ancient healing practice of Reiki (Rei “guided” Ki “life force energy”). This rejuvenating process involves the hands being placed just off the body, or lightly touching the body which brings about feelings of clarity & peace of mind, release of heavy emotions, improved sleep quality, and increased energy.
Price: $135 plus tax/gratuity
*Available in select rooms.
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Reflexology Session
1 Hour Reflexology Session
Promote self-healing with our specialized 1 hour Reflexology Session! The advanced thumb and finger techniques utilized apply pressure to specific areas of the feet, stimulating the neural pathways throughout your body.
Price: $135 plus tax/gratuity
*Available in select rooms.
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