A Magical Eastern Shore Holiday Season

With the holiday season right around the corner, it’s the perfect time to plan a little R&R into your busy schedule for a mid-season pick-me-up for this year’s festivities. Great Oak Manor on the Chesapeake Bay is the perfect destination for a magical East Coast Holiday. Join us at our waterfront Chestertown, Maryland bed and breakfast for a getaway you’ll never forget.

Thanksgiving Dinner at Great Oak ManorDinner without the Dishes

If you are joining us on Thanksgiving, Christmas or New Year’s, enjoy a traditional holiday meal with all of the delicious fixings! We also offer private dinners (when given 72-hours advanced notice), and Soup-er Suppers featuring a hot bowl of soup, chili, or stew of the chef’s choice, corn muffins, salad, a slice of pie and a glass of wine. You are sure to feel the comfort of the holidays with every bite.

Manager’s Wine Hour

The holidays are filled with moments to share stories and delicious treats, and here at the Manor it is no different. Every Friday evening, we host a Manager’s Wine Hour. Join your innkeepers and fellow guests in enjoying hors d’oeuvres and wine from Crow Vineyard Winery, and toast to the season!

Living Room during Holiday Vacation at Great Oak Manor

Sipping by the Fire

There is no better time to cozy up inside than when the temperatures start to drop and the leaves start to fall. Great Oak Manor guests are always welcome to a specially curated selection of wine, coffee, and tea by the fire in the library as well as other luxurious amenities.

Holiday Shopping

Historic downtown Chestertown is the best place to find unique holiday items and check off those on your shopping list. Explore Twigs and Teacups to find clever gifts, fun toys, and more amusements. Stop into Chester River Wine & Cheese Co for a wonderful selection of wines, cheeses, meats, and other kitchen accessories. Or peruse Bookplate to appease your most imaginative reader. The possibilities are both unique and endless.

Holiday Shopping in Chestertown MD

A Dickens of a Christmas

December 7-9, 2018, the city of Chestertown lights up for a Victorian Holiday Extravaganza. Don’t miss your chance to join in on the festivities of A Dickens of a Christmas. There will be a festive kick-off party “Ebenezer’s Soiree”, Carolers, House Tours of Chestertown’s Finest Victorian and Historic Homes, Pictures with Santa, Crafts, Flavours of England, Beer, Bonfires and more!

The Holiday Spirit

A relaxing stay at Great Oak Manor is sure to put you in the holiday spirit. You’ll start your day with a delicious full breakfast featuring seasonal fresh fruit, homemade baked goods, a tasty hot entrée and more. Then end your night in one of our 12 romantic guest rooms with individual highlights such as a cozy fireplace, a spacious bath with skylight, inviting French doors, or a rich red bathroom. Your Chesapeake Bay vacation is sure to be magical.

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