Christmas in Woodstock, Winter in Vermont

Experience the Best of a Woodstock, Vermont Christmas!

11/10/2022
Enjoy the magical of a Woodstock, Vermont Christmas while shopping downtown, where the stores are dressed for the season

If you haven’t had the pleasure of experiencing a Woodstock, Vermont Christmas, let us introduce you to the sheer magic of the season this year. Old-fashioned holiday charm takes over the shops and businesses lining Central Street in downtown Woodstock, and holiday events keep the atmosphere bright, festive, and filled with joy. There is simply nowhere more beautiful than a Woodstock, Vermont Christmas.

Your headquarters for all things festive – not to mention romantic and relaxing – is the Jackson House Inn, the leading Woodstock, VT Hotel. We offer an intimate guest experience that remains unmatched in this storybook Vermont town. We’d love to treat you to a relaxing getaway while enjoying the best of this holiday season.

Start (or finish) your holiday shopping in beautiful downtown Woodstock, join in the festivities during the annual Wassail Weekend, participate in some authentic Victorian Christmas Traditions at The Christmas on the Farm event at nearby Billings Farm, and otherwise, treat yourself to a few days of quiet luxury at our Four Diamond Woodstock, VT Hotel this holiday season. Book your room today!

The popular Wassail Weekend is One of the best ways to celebrate a Woodstock, Vermont Christmas

Enjoy the Best of the Woodstock, Vermont Christmas Season

If you’re looking for a postcard-worthy destination to get into the holiday spirit, then you don’t want to miss a Woodstock, Vermont Christmas. The entire village gets dressed up for the season with lights all aglow and fresh greens adorning doorways and fences. Once the snow begins to fall in earnest this winter, the village is transformed into something straight out of a snow globe or a print by Currier & Ives.

What could be more true to the Woodstock holiday experience than holiday shopping? Downtown Woodstock’s Central Street is always a fun place to shop, but the experience is magnified by the gentle glow of holiday lights and decorations. Replete with small, locally owned businesses and one-of-a-kind offerings, you’re sure to find something extraordinary for everyone on your holiday lists this year. Favorite stores include:

Our most talented local artisans and makers are to be found just outside downtown Woodstock, including Farmhouse Pottery, Simon Pearce, and Shackleton Thomas.

Shopping and pretty lights aren’t all a Woodstock, Vermont Christmas has in store for you, though. The season is also packed with fun events, including the best of them all, Woodstock’s popular Wassail Weekend. Woodstock’s Wassail Weekend is one of the most festive weekends of the year and is traditionally held on the second weekend of December; in 2022, the event dates are December 9 to 11.

You can feel the joy everywhere you turn throughout this festive weekend, amplified by the warm, twinkling lights of the season, the historic decorated homes, and the joyous sounds of the season. There are events all over town, including a festive parade and Victorian-themed fun at the Billings Farm. The Billings Farm also hosts its annual¬†Christmas at the Farm celebrations throughout the Woodstock, Vermont Christmas season, where you’ll enjoy the charms and traditions of a traditional Victorian Christmas.

Finally, no Woodstock, Vermont Christmas season would be complete without taking in the breathtaking winter landscapes you’ll find around every bend, the perfect backdrop for various outdoor adventures.

From cross-country skiing and snowshoeing at the Woodstock Nordic Center or downhill skiing at the Saskadena Six (our super local mountain) or Killington to dashing through the snow behind a horse-drawn carriage and ice skating, it’s easy to find a fun snow-laden adventure or two while you’re visiting our Woodstock, VT hotel.

Relax and unwind by the fire while celebrating the magic of a Woodstock, Vermont Christmas with us at the #1-rated Woodstock, VT Hotel

Savor the Moment at our Woodstock, VT Hotel

As you can see, there is plenty to do and see during the Woodstock, Vermont Christmas season, ad there’s nowhere better to serve as your home away from home than in the quiet luxury and sophistication of our Woodstock, VT hotel. The Jackson House Inn offers an unparalleled guest experience – and you’ll see and feel the difference the moment you pull up in front of our historic Inn.

We offer various accommodations at the hotel, each thoughtfully designed and appointed with our guests’ comfort in mind. Whether you choose one of our spacious fireplace suites or our classic rooms, you’ll find each one features fine antiques, beautiful works of art, and luxurious touches like Frette linens and Anichini bed coverings. These individual touches embody our commitment to getting the details right for your comfort.

Each morning of your stay, you’ll be treated to a sumptuous and decadent breakfast made from scratch by our exceptional chefs. Although we can accommodate dietary restrictions with advance notice, we invite you to let us take you on a curated culinary journey each morning of your stay.

After a day of enjoying the best of the Woodstock, Vermont Christmas season in town, we invite you to return to our intimate hotel each afternoon for a delicious cocktail, glass of wine, or Vermont craft beer from the special selection in our Tavern. Drinks can be enjoyed in one of our cozy common areas or outside bundled up with a blanket by our cozy outdoor firepit.

Transform your getaway from ordinary to extraordinary this winter, and celebrate a Woodstock, Vermont Christmas in style with the Jackson House Inn. Book your room at our Woodstock, VT hotel today!

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Give The Gift of Jackson House This Holiday Season

Give your loved one an exceptional gift of a stay at Jackson House Inn.  We offer gift certificates in many amounts.