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Woodstock Hotels & Vacation Rentals for Christmas

Woodstock
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$100 - $199
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Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Enjoy Traditional New England Christmas in Woodstock, Vermont

Woodstock hotels for Christmas tend to be busy, as this quaint Vermont town overflows with holiday cheer. Earlier in December, the annual Wassail Weekend sees the town overtaken by revelers in 19th century period costumes, complete with riders on horseback. If you can't make the parade and all that Wassail Weekend entails, there's still much to enjoy the rest of the month, however. Woodstock vacation rentals for Christmas let you experience a quintessential New England holiday, from crisp ski slopes to covered bridges glittering with Christmas lights.

Christmas in Woodstock: Top Accommodations

Condo Woodstock
Dec 19 - Dec 26
$283 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.5
"Outstanding" (14 ratings)
Woodstock, Windsor County, Vermont, United States
Details
The Killington Group
View deal
Condo Woodstock
Dec 19 - Dec 26
$233 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.2
"Very good" (14 ratings)
Woodstock, Windsor County, Vermont, United States
Details
The Killington Group
View deal
Condo Woodstock
Dec 19 - Dec 26
$732 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.7
"Outstanding" (3 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
Details
Killington Vacation Rentals
View deal

Where to Dine for Christmas in Woodstock

Surrounded by rich Vermont farmland, Woodstock's restaurants benefit from fresh ingredients and long-standing food traditions. Charming, cozy interiors simply complete the picture. Many restaurants will be closed on Christmas Day itself, so be sure to call ahead. However, the restaurants at local inns tend to stay open for the afternoon.

  • Worthy Kitchen

    Aptly named, this farm-to-table restaurant is known for its superb Christmastime comfort food, showcasing local ingredients. With 18 craft beers on tap, and divine doughnuts served hot, you'll won't need much excuse to indulge.

  • Melaza Bistro

    Chef David Diaz brings a symphony of Caribbean fusion flavors to the table. Enjoy a unique experience at this tapas spot.

  • Bentley's Restaurant

    Warm up at this traditional restaurant right in downtown Woodstock. Bentley's serves traditional Christmas fare in tastefully decorated, homespun surroundings.

  • The Quechee Inn

    In the neighboring town of Quechee, check out the restaurant at this charming inn for traditional Christmas Day fare.

Best Places to Stay for Christmas in Woodstock

Condo Woodstock
Dec 19 - Dec 26
$507 per night
Condo ∙ 6 guests ∙ 1 bedroom
5.0
"Excellent" (18 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
Details
Killington Vacation Rentals
View deal
Apartment Woodstock
Dec 19 - Dec 26
$909 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.3
"Very good" (70 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
Details
travelstaytion
View deal
Condo Woodstock
Dec 19 - Dec 26
$300 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.7
"Outstanding" (19 ratings)
Woodstock, Windsor County, Vermont, United States
Details
The Killington Group
View deal

Best Winter Activities During the Holidays in Woodstock

New England attracts skiing aficionados thanks to its powdery slopes and crisp, clean air. America's first ski tow opened at Gilbert's Hill in Woodstock in 1934. Today, the town is a portal to the best skiing in the Northeast. Jay Peak, Sugarbush, Smuggler's Notch, and Okemo Mountain await when you choose Woodstock hotels for Christmas. Of course, there's also plenty to do right in town.

  • Skiing in Vermont

    Woodstock vacation rentals for Christmas appeal to serious skiers and fans of snowball fights alike. Hike Mount Tom for a spectacular view of Woodstock's twinkling lights. Back country trails ribbon through the hills surrounding the town, including 555 acres of Mount Tom forest, part of the Marsh-Billings-Rockefeller National Historical Park.

  • Toast s'mores on the Yule Log Fire

    Part of Wassail Weekend, visitors gather along with locals to stand around a fire on the village green, and listen to choral songs while roasting chestnuts and s'mores.

  • Christmas shopping on Main Street

    The independent boutiques that line Woodstock's Main Street are inviting and quaint. Cozy cafes make Woodstock's downtown district an even bigger draw. Visit F.H. Gillingham & Sons, open since 1886. It's a shopper's dream if you are looking for local maple syrup, jams, and other souvenirs.

Recommended Accommodations for Christmas in Woodstock

Condo Woodstock
Dec 19 - Dec 26
$283 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.5
"Outstanding" (14 ratings)
Woodstock, Windsor County, Vermont, United States
Details
The Killington Group
View deal
Condo Woodstock
Dec 19 - Dec 26
$233 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.2
"Very good" (14 ratings)
Woodstock, Windsor County, Vermont, United States
Details
The Killington Group
View deal
Condo Woodstock
Dec 19 - Dec 26
$732 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.7
"Outstanding" (3 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
Details
Killington Vacation Rentals
View deal

Things to Do With Your Family During Christmas Vacation in Woodstock

Whether it's jazz performances and a reading of Dylan Thomas's "A Child's Christmas in Wales" during Wassail Weekend, or a chorus of traditional carols by candlelight, your family will be left rapt by Christmas in Woodstock. Here are some of the most engaging events for little ones:

  • Christmas Wassail Feast

    A part of Wassail Weekend, local high school actors attired in imaginative medieval costumes entertain visitors at the celebrated Christmas medieval feast. Dine on period dishes while jesters cavort around you and kings preside over the proceedings. You'll even toast the season with a child-friendly version of the traditional mulled ale.

  • Christmas Parade

    At the center of Woodstock's Wassail Weekend is the Christmas Parade. Riders attired in traditional costume and Christmas colors ride beneath the snow-laden boughs of trees. Hundreds flood this small town's streets to watch the spectacle, wave to Santa, and rally the marching bands as they pass joyfully through town.

  • Billings Farm

    Just outside town, in bucolic surrounding scenery, you'll find Billings Farm, where you can enjoy excellent seasonal farm-to-table fare. Signature Christmas at the Farm events throughout December offer an insight into 19th century living and feature baked treats from the kitchens. Enjoy a sleigh ride around the estate's heritage sites, and visit the farm museum. Bedecked in seasonal finery, the farm is an especially picturesque place, snuggled in the snowy hills of Vermont.

  • Sleigh rides

    Take a horse drawn sleigh beneath pretty covered bridges hung with Christmas lights, to explore swathes of snow-kissed landscape. Kedron Valley Stables offers private sleigh rides you can arrange in advance.

Top Offers for Christmas in Woodstock

Condo Woodstock
Dec 19 - Dec 26
$507 per night
Condo ∙ 6 guests ∙ 1 bedroom
5.0
"Excellent" (18 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
Details
Killington Vacation Rentals
View deal
Apartment Woodstock
Dec 19 - Dec 26
$909 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.3
"Very good" (70 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
Details
travelstaytion
View deal
Condo Woodstock
Dec 19 - Dec 26
$300 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.7
"Outstanding" (19 ratings)
Woodstock, Windsor County, Vermont, United States
Details
The Killington Group
View deal

Frequently Asked Questions

How much do vacation rentals for Woodstock Hotels & Vacation Rentals for Christmas cost?

HomeToGo has incredible rentals for Woodstock Hotels & Vacation Rentals for Christmas, with prices as low as $144 per night.

What kinds of rentals can I find for Woodstock Hotels & Vacation Rentals for Christmas?

There are many Bed & Breakfast rentals and Apartment rentals that are great for Woodstock Hotels & Vacation Rentals for Christmas.

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