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 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 private, romantic dinner for two including a bottle of Crow Vineyard wine. Your special dinner will be prepared by our chef to your liking.
Day Two – Explore & Savor
- Enjoy a scrumptious breakfast either in our safe dining room or in your own room complete 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 or in your room complete with a sunny Mimosa.
- Take advantage of late check-out at noon and leave with a bag of our homemade manor house cookies for your trip home.
Price: $550
New reservations only. Cannot be combined with any other offers or third party specials. Room not included in package price.
Fireside Dinner
Feast on this decadent meal, including:
- Seasonal Appetizer
- Spinach or Caesar Salad
- Your choice of two “Surf & Turf” entrées ~ Filet Mignon with Wild Mushroom Demi Glace, Our Own Jumbo Lump Crab Cake with Remoulade Sauce, Chicken Chesapeake, Vegetable Risotto
- Rosemary Roasted Potato, Rice Pilaf, or Grilled Polenta
- Roasted Green Beans with Shallots and Parmesan or Saute of Mixed Seasonal Vegetables in Herb Butter
- Dessert
- Beer & Wine Available for Purchase
Price: $150 per couple
Whenever possible, we strive to use fresh, local and/or organic products in support of our farmers and watermen.
Saturday Night Supper
Enjoy a delicious meal of:
- Grilled steak, catch of the day, chef’s choice chicken, or polenta with wild mushrooms
- Manor House Garden Salad or Seasonal Vegetables
- Dessert
- Beer and wine available for purchase
Price: $49.95 per person plus tax and gratuity
Whenever possible, we strive to use fresh, local and/or organic products in support of our farmers and watermen.
Souper-Supper
This winter, cozy up on crisp winter days and savor yummy eats and sip delicious wine in our elegant dining room or romantic library.
Souper-Suppers include a hearty soup or chili of the day, salad, and a corn muffin or bread.
Price: $25 per person plus service fee and tax
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:
- Bottle of sparkling wine (for mimosas – orange juice included)
- Cooking class with a meal
- Wine tasting at Crow Vineyards and Winery
- Stocked fridge for in house breakfast
- We keep the woodbox stocked with firewood
Price: $99 per person plus room rate
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: $149
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
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.
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!
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.