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 (Warm Weather Edition)

Day One – Arrive & Relax

  • Arrive at 1:00pm for an early check-in. You will be welcomed with a chilled bottle of Pinot Gris and a cheese and charcuterie board prepared by our staff.
  • Take a stroll around the property and down to our private beach. Enjoy a Chesapeake Bay water experience. We provide kayaks, paddle boards and a canoe for exploring Fairlee Creek and out into the Chesapeake Bay. We also have life vests and beach towels. Or, perhaps, use our cruisers for a nice bike ride in the countryside.
  • For the ultimate Eastern Shore Experience, enjoy a crab feast for two featuring 1dz Maryland blue crabs. If you don’t know how to pick crab, our experienced staff will teach you. A bottle of white wine or a 6-pack of beer is included. We will set you up in our Gazebo right on the Bay and then clean up after you!

Day Two – Indulge & Enjoy

  • Enjoy a scrumptious breakfast-with-a-view outside on the porch, patio or lawn bistro tables complete with our signature Bloody Mary.
  • A wine tasting at Crow Winery and Vineyard for the late morning or afternoon. We will coordinate for you. Enjoy Crow’s award winning wines with a light lunch. Or, wine tasting at Casa Carmen in their Chestertown tasting room to include tapas for a light lunch.
  • Have a wonderful dinner out at one of our top favorite restaurants. We will happily make your reservation and will supply a $100 voucher to use.
  • Return to the Manor for dessert – s’mores on the beach bonfire area. Enjoy the sunset and the Bay breezes.

Day Three – Savor Breakfast & Check Out

  • Enjoy another scrumptious breakfast-with-a-view complete with a sunny Mimosa.
  • Enjoy a late check-out at noon and leave with a bag of our homemade Manor house cookies for your trip home.

Price: $599 plus tax and $75 gratuity

New reservations only. Available May-October 2021. Cannot be combined with any other offers or third party specials. Room not included in package price.

No refund on any parts not used.

Blue Crab Chesapeake Charters Sunset Sail Package

Interested in setting sail on the Chesapeake?

Let us know in advance with this package and we’ll have your vouchers all ready for you upon check-in.

  • We make your reservations on Island Girl by Blue Crab Chesapeake Charters
  • Enjoy 1 ½ hour sail from the Rock Hall Harbor and out onto the Bay to view our amazing sunsets
  • Wine and Cheese basket goes with you by the GOM staff

Price: $145

Available April through October 1st.

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/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: $149

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 white wine

Price: $145 plus tax and service fee

Available May 1- October 15

A pound of shrimp can be added for an additional fee.


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

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!

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.

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
Picnic on the beach

Let’s Picnic

A delicious picnic meal to enjoy at the Manor or while out adventuring