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.


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.

Red wine being poured into a glass

Red Wines

Up the romance with red wine from an award-winning local vineyard.
Glass of white wine in a vineyard

White Wines

Enjoy a bottle of locally-sourced, award-winning white wine.
roasting s'mores

S’mores Kit for 2

We provide the ingredients and the fire, you provide your cooking skills.
Fruit and cheese plate

Cheese Anyone?

A cheese and fruit tray and a bottle of wine ready in your room
Bouquet of flowers

Flower Arrangement

Beautifully arranged flowers waiting in your room
60 Minute Massage at Great Oak Manor

60 Minute Massage

Rejuvenate with a refreshing 60 minute massage
Reiki Session at Great Oak Manor

Reiki Session

Experience the ancient healing practice of Reiki
Reflexology Foot Massage at Great Oak Manor

Reflexology Session

Promote self-healing with our specialized 1 hour Reflexology Session