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
Honeymoon Package
Start your happily ever after at our romantic Maryland bed and breakfast. Enjoy your stay with the following special details:
- Two soft and luxurious Great Oak Manor bathrobes
- Two exclusive pottery mugs to take home with you
- A scrumptious breakfast served to you in-room, complete with Champagne
Price: $325
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)
~or~
$125/person on weekends (Saturday – Sunday) and Federal Holidays
Packages include golf cart, rental clubs, lunch, a draft beer or fountain soda.
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 Wines
Red Wines
Add some romance to your stay with a bottle of red wine from our neighbors at Crow Vineyards, winners of gold international wine awards and the Maryland Governor’s Cup status for three years running.
Choose from either the Rosé at $31 a bottle or the Barbera at $42 per bottle, and let the romance begin!
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White Wines
White Wines
As three-year winners of gold status at international competitions and the Maryland Governor’s Cup status, our neighbors at Crow Vineyard takes their wine seriously, just like we know you will seriously enjoy these wines!
Choose from either the Vidal Blanc at $29 per bottle or the Vintner’s Select White Blend at $22 per bottle.
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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. A bottle of wine can be purchased.
Price: $125/couple plus tax and gratuity
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Cheese Anyone?
Cheese & Wine 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
- Bottle of wine
Price: $70
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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