Discover a selection of 1,000 vacation rentals in Woodstock, VT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $146 per night, and houses and cabins are popular options for a stay in Woodstock. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Woodstock
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Destination guide

Just a little bit different than that other Woodstock

Like much of Vermont, this Woodstock is certainly earthy and crunchy, but it's not quite as boho as the Woodstock you're thinking of. Instead of daisy chains and peace signs, Vermont's version features a backdrop of mountains and rivers that could be from a painting. Skiing and hiking are the main activities here, but Woodstock manages to cater to both luxury travelers, and those looking for a quaint escape. Opt for a Woodstock vacation rental that feels like a true home away from home, and by the end you might be daring yourself to leave.

Things to do

Where ski bunnies and nature nerds converge

Woodstock is an easy drive from Killington Resort, which offers some of the best skiing in the region. Indoor sports lovers, however, might prefer the Union Arena Community Center, which features a state-of-the-art ice skating rink (plus loads of other events and performances). Head to the VINS Nature Center for the planetarium, nature camps, and bird rehabilitation, and then take your newfound knowledge out into the wild at a nearby state or national park. If you can't get enough of the local history and culture, make sure the galleries and specialty museums all make it on your list, too.

Activities

Any chance 80s ski style is making a comeback?

In Vermont, you're never too far from a ski resort, so pack for your Woodstock vacation rental with fresh pow in mind. Or, should you visit when the temps are more mellow, plan for hiking, biking, and camping through the mountains. Birdlovers can happily spy on their feathered friends in the wild, or at the local wildlife rehabilition center. The insanely charming town center also features a local community center with festivals, performances, and sporting events, as well as plenty of shops, galleries, and restaurants to suit your fancy. Most importantly, don't miss the bar scene, perfect for apres-ski festivities.

Weather

Here, Woodstock is in season every season

For most travelers, Woodstock, like much of Vermont, is strictly a winter destination. But think outside the seasonal box! Winter might be the obvious time to head deep into ski country, but there are perks to the area all year long. Enjoy the wildflowers that pop up in spring, or spend a summer day exploring life on the lake or in the river. Visitors in fall should pick a Woodstock vacation rental in the woods for optimal leaf-peeping -- just don't forget your camera!

Natural features

In Woodstock, an uphill climb is a good thing

With so much to do outdoors, nature lovers will find it impossible to pick exactly what to see. From walks in the forest, spotting deer on the ground and hawks in the sky, to getting up close at the local wildlife refuge center, there's much to learn in Woodstock. If animals don't strike your fancy, then perhaps picking wildflowers, walking along the creek, or floating around the lake or down the river will be more your speed? Speaking of speed, downhill skiiers can spend a full day on ski runs and still be ready for more.

How to get there

How to get to and around Woodstock

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.5 mi (16.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Springfield, VT (VSF-Hartness State), which is 19.5 mi (31.4 km) away.

How many vacation rentals are available around Woodstock, VT?

Our 2021 property listings offer a large selection of 808 vacation rentals around Woodstock. From 399 house rentals to 54 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Woodstock?

Vrbo offers a large selection of vacation rentals near lovely places in Woodstock. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Marsh-Billings-Rockefeller National Historical Park: 1,201 vacation rentals
  • Woodstock Country Club: 1,225 vacation rentals
  • Woodstock Town Hall Theatre: 1,220 vacation rentals
  • Billings Farm and Museum: 1,152 vacation rentals
  • Ottaquechee River: 1,231 vacation rentals

But there are many other points of interest around Woodstock listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Woodstock?

Yes, of course. Vrbo has 399 Houses in Woodstock. Our other popular types of vacation rentals in Woodstock include:

  • Cabins: 54 rentals available
  • Cottages: 36 rentals available
  • Chalets: 14 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Farmhouses and more.

Can I find a vacation rental with pool in Woodstock?

Yes, you can select your preferred vacation rental with pool among our 401 vacation rentals with pool available in Woodstock. Please use our search bar to access the selection of vacation rentals available.