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.
Day Two – Explore & Savor
- Enjoy a scrumptious breakfast either in our safe dining room with our signature Bloody Mary.
- Pick up your picnic lunch to take with you while you explore Chestertown and Kent County. Your TouchStay App will guide you.
- Savor dinner out at one of our top restaurants. We will supply a $100 voucher to use.
Day Three – Fuel Up & Head Home
- Wake to another full breakfast in the dining room complete with a sunny Mimosa.
Price: $550 plus tax and $75 service fee
New reservations only. Cannot be combined with any other offers or third party specials. Room not included in package price.
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
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
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
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.
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.