Why You Need to Visit Maryland’s Eastern Shore after the Holidays

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The holidays are here again. For the next few weeks, you’ll spend your free hours decorating the tree, baking cookies, squinting at the computer screen as you search Amazon or Wayfair for the perfect gifts, reminding your (grand)children that Santa is watching them, shopping for holiday food, gift wrap, and other supplies, and wrapping an endless pile of presents. The list of holiday tasks is endless and then when the day is finally over, you’re an exhausted mess.

You deserve a mini-break. You know you do. So, treat yourself to a few days on the Chesapeake Bay after the holiday.

Need some convincing? Here are a few reasons to visit Great Oak Manor:

Chestertown Waterfront

  • Chestertown is a unique, historic town with great restaurants, tons of shopping, and a rich history. Its brick sidewalks, elaborate architecture, and antique stores beckon visitors all year long.
  • First Fridays in Chestertown are like a little party for the town. Enjoy the festivities as you eat, drink, and shop at the charming stores and boutiques.
  • The Chesapeake Wine Trail, which can be quite busy over the summer, has quieted, leaving you with plenty of time to chat with the winemakers and other staff at the vineyards. Crow Vineyard and Winery, Clovelly Vineyards, and Cassinelli Winery & Vineyards are all located in Kent County and are a short driving distance from the Manor.
  • Eastern Neck National Wildlife Refuge is a 2285 acre island that provides habitat for various wildlife including small mammals and more than 240 species of birds, one of which is the Tundra Swan. These graceful creatures arrive in late November for a visit before traveling more than 4,000 miles in the spring.

    Tundra Swan

  • No matter the season, the Chesapeake Bay has the most glorious sunsets!

Great Oak Manor has the following specials:

New Year’s

Enjoy a peaceful retreat after the hustle and bustle of the holidays. Guests staying three nights receive a complimentary dinner with wine.

Mid-Week Special*

Buy one night, get the second 50% off!
Code: BOGO

Buy two nights, get the third free!
Code: Fireside

Call us at 410-778-5934 or book online today.


Stay tuned for more information on the following events:

Martin Luther King Jr. Day
Valentine’s Day
President’s Day






*Sunday to Thursday only. New reservations only. Not to be combined with other offers. Second-floor rooms and Carriage House only; rooms subject to availability. Offer valid December 2017 – January 2018.

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