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.

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: $99

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

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 wine

Price: $145

A pound of shrimp can be added for an additional fee. Available April through October 31st.

Spring Wellness Retreat with River Warrior Yoga

Don’t wait to feel great! Join us March 27-29 and put the spring back in your step with a wonderful weekend of wellness, led by River Warrior Yoga. Enjoy the benefits of winter hibernation alongside the blossoming effects of spring! You will be guided through both yoga and meditation and will have the opportunity to enjoy massages, reiki, reflexology, nature walks, scenic sunsets, heated floors, customized health eating packages, and even more.

The Earlier You Book, The More You Save!

  • $300 by February 15th, Use Code SPRING300
  • $375 by March 1st, Use Code SPRING375
  • $450 by March 27th, Use Code SPRING450

Early bird rates are for the retreat only and are not inclusive of accommodations.

Plus Save 25% On Your Room!

  • Rooms are first-come, first-served! Hurry and reserve your favorite room while it’s still available and enjoy 25% off during this retreat.
  • Room reservations must be made separately by phone. Call Holly McKee at (410) 778-5943 to book.
  • Add a customized healthy eating package for $125.

Cozy Mid-Week Winter Special

What is more romantic than a cozy winter stay in Chesapeake Bay? Grab your loved one and save big this holiday season with our mid-week special. For every night you stay, get a percentage off your room starting with 10% off the first night, 25% off the second night, 33% off the third night of your stay. Use promo codes: MidweekWinter-1; MidweekWinter-2; MidweekWinter-3

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.
Private Dinner for Two

Private Dinner for Two

Enjoy a very special evening without having to leave the property!
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