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.
The Ultimate Cozy Getaway to the Bay
Day One – Arrive & Unwind
- Arrive at 1pm for an early check-in and be welcomed with a chilled bottle of Pinot Gris and a cheese and charcuterie board prepared by our chef.
- Take a stroll around the property and down to our private beach. In season, we provide kayaks, paddle boards and a canoe for exploring Fairlee Creek and out into the Chesapeake Bay.
- Freshen up and come to our dining room for a wonderful and tasty Italian dinner for two including a bottle of Crow Vineyard wine.
Romance/Anniversary 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: $159
Girls’ Getaway Package
Get a group of friends together for a relaxing stay in our Carriage House, with majestic views of Chesapeake Bay and room for 4 to 6 people. Book two or more nights, and enjoy all of the following during your stay:
- Champagne Breakfast
- Charcuterie Board
- Wine tasting at Crow Vineyards and Winery
- Private firept fun with s’mores
- We keep the woodbox stocked with firewood
Price: $99 per person plus tax and room rate
Pet Perks Package
Bring your pup and they can enjoy these wonderful perks:
- Cozy Pet Bed
- Warm Blanket
- Feeding & Water Bowls
- Fun Toys
- Tasty Treats
- A Note from Lizzie the Manor Dog Welcoming Them
- On-Site Pet Station with Bags and Disposal of Waste
Price: $25 per night
*Pet fee is included in the pet package
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
Winter Weekday Special
Get away to Chestertown this December and save 25% on your cozy winter escape! Book 2 or more nights Sunday-Thursday to apply the discount.
Book with Promo Code: ND2021
New reservations only. Available for Hodges, Roese, Sterling, Russell, Caulk, Tylden, Wickes, D’Oench, and Marmaduke suites. Must book and stay by December 30, 2021, December 24-25, 2021 are excluded. Cannot be combined with other discounts.
Early Bird Check-In
If you would like to kick off your vacation early by a few hours, we offer early check-in for an additional $25 per hour. So grab your suitcase and start your getaway early!
Limited to Manor rooms only.
Sleep In and Check-Out Late
Stay cozy in bed with your loved one for a little bit longer by extending your stay. We offer late check-out for an additional $25 per hour.
Limited to Manor rooms 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 10% 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 per bottle, the Vintner’s Select Red at $37per 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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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: $70 plus tax
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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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Let’s Picnic
Let’s Picnic
Sometimes you arrive and don’t want to go back out for lunch or dinner. This way, you can enjoy a picnic meal on the beach, take it with you kayaking, or have a sunset picnic on the bluff.
- Delicious fresh sandwiches with a choice of Chicken salad or Tuna Salad
- Potato Chips
- Homemade sweet snack of the day
- Fresh Fruit
- Soft drinks or water
Price: $49 plus tax and service fee