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Woodstock Hotels & Vacation Rentals for Christmas

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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
$584 per night
Condo ∙ 8 guests ∙ 2 bedrooms

Condo in Killington with Pool & Grill

5.0
Outstanding (4 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
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Condo Woodstock
Dec 19 - Dec 26
$386 per night
Condo ∙ 4 guests ∙ 1 bedroom

Wonderful Condo in Killington with Yard, Grill & Pool

5.0
Outstanding (4 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
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Condo Woodstock
Dec 19 - Dec 26
$263 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Killington with Pool

5.0
Outstanding (17 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
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Where to Dine for Christmas in Woodstock

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.

  • 1. 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.

  • 2. Melaza Bistro

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

  • 3. Bentley's Restaurant

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

  • 4. 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

Apartment Woodstock
Dec 19 - Dec 26
$199 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental Apartment in Killington with Pool

Woodstock, Windsor County, Vermont, United States
Free cancellation
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House Woodstock
Dec 19 - Dec 26
$1,377 per night
House ∙ 14 guests ∙ 5 bedrooms

House in Killington with Grill, Sauna, Hot Tub

Woodstock, Windsor County, Vermont, United States
Free cancellation
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Condo Woodstock
Dec 19 - Dec 26
$363 per night
Condo ∙ 6 guests ∙ 1 bedroom

Condo in Killington with Yard, Pool & Grill

4.6
Excellent (7 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
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Best Winter Activities During the Holidays in Woodstock

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.

  • 1. 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.

  • 2. 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.

  • 3. 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

House Woodstock
Dec 19 - Dec 26
$951 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Ludlow with Grill

Woodstock, Windsor County, Vermont, United States
Free cancellation
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Villa Woodstock
Dec 19 - Dec 26
$401 per night
Villa ∙ 6 guests ∙ 2 bedrooms

Nice Villa in Brownsville with Outdoor Pool + Panoramic Views

Woodstock, Windsor County, Vermont, United States
Free cancellation
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Condo Woodstock
Dec 20 - Dec 27
-19%
$890
$724 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Killington with Wood-Burning Fireplace

4.8
Outstanding (79 ratings)
Woodstock, Windsor County, Vermont, United States
Very popular
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Things to Do With Your Family During Christmas Vacation in Woodstock

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:

  • 1. 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.

  • 2. 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.

  • 3. 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.

  • 4. 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

House Woodstock
Dec 19 - Dec 26
$492 per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation Home in Killington

5.0
Outstanding (7 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
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Condo Woodstock
Dec 19 - Dec 26
$644 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Killington with Sauna + Mountain Views

Woodstock, Windsor County, Vermont, United States
Free cancellation
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House Woodstock
Dec 19 - Dec 26
$1,314 per night
House ∙ 16 guests ∙ 6 bedrooms

Vacation Home in Killington with Grill, Yard & Patio

4.7
Excellent (6 ratings)
Woodstock, Windsor County, Vermont, United States
Free cancellation
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Information about Woodstock Hotels & Vacation Rentals for Christmas

💳 Highest rates in October
😎 Least busy month July
🛏️ Popular home types House rental and Bed and breakfast rental
🌡️ Hottest months July and August
❄️ Coldest months 12 °F in January and February
🌧️ Rainiest months 19 rainy days in December and January

Frequently Asked Questions

Woodstock Hotels & Vacation Rentals for Christmas: What is the nightly price for a stay?

HomeToGo offers great vacation rentals, with rates as low as $154 per night.

Woodstock Hotels & Vacation Rentals for Christmas: what kinds of vacation rentals are available in Woodstock?

You can find 22 House rentals and 43 Bed and breakfast rentals in Woodstock on HomeToGo.

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