Small Town
Holiday Getaways
Celebrate the holidays at The Chesapeake Inn! There is no better place to experience a classic, traditional, small-town, family-friendly Memorial Day, Fourth of July, Labor Day or Christmas season than Urbanna, Virginia. For example every weekend in the December, The Inn is decorated and there is something exciting planned in our historic portside town which you can explore from your cozy, luxurious room at our little inn. Return here often for updates as the holidays near!
Check out our local happenings to see what’s coming up in Urbanna - and experience it all from the Chesapeake Inn!
Between holiday happenings
Stroll the streets and shop for gifts without the crowds in Urbanna’s many boutiques, including Ballgown Barefoot, Low Tide, The Gilded Crown, Urbanna Trading Company, ReSail Boutique, Bristow’s and more. From the latest fashions to beautiful antiques to gourmet treats, Urbanna’s shops offer it all.
And between shopping, enjoy hot chocolate and a warm meal – maybe even locally farmed roasted oysters! – at the town’s many restaurants, such as Portside Grill, Somethin’ Different, The Wooden Pickle, Little Jimmy’s, or Mi Jalesco. And soak up the winter skies and sea breezes from the Town Marina, Waterman’s Park; often it is still warm enough to take a kayak out, or at least explore town in one of our signature surreys or bikes.
In the center of downtown Urbanna
The Chesapeake Inn offers the perfect home base for exploring the town’s many holiday offerings. And of course our halls will be decked and Santa will make multiple appearances! Book your Urbanna holiday stay today!
