Discover a selection of 500 vacation rentals in Woodstock 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 kitchens and swimming pools. Prices start at $197 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.
AsyncDestinationUrgency
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
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?

Our 2020 property listings offer a large selection of 721 vacation rentals around Woodstock. From 304 house rentals to 28 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Village of Woodstock?

Nestle yourself and your group high up in the mountains and get set for enthralling sunrises, excellent stargazing and tons of fresh air. Vrbo has no less than 366 mountain vacation properties available. Alternatively, you might like to go for a different sort of setting. Vrbo has oodles of properties to choose from, including:

  • 248 resort vacation rentals.
  • 245 mountainside vacation rentals.
  • 179 ski-in vacation rentals.

Can I rent a house in Village of Woodstock?

Rather than staying in a cookie-cutter, chain hotel room this vacation, you could rent a whole house. You'll feel like part of the neighborhood before you know it! There are 347 houses currently on Vrbo. Prices start from $107 per night. Or maybe you'd prefer one of the area's other rental options, such as:

  • Bed & breakfast: 16 vacation homes. Prices start from $189 per night.
  • Hotel: 15 vacation homes. Prices start from $89 per night.
  • Cottage: 9 vacation homes. Prices start from $197 per night.

Can I stay in Village of Woodstock in a large group?

Sometimes it can be tough finding time to unwind with your closest family and friends. A trip away is a fantastic opportunity to come together. If you were planning to stay under the same roof, Vrbo has options. Presently, condo vacation homes are preferred for big groups of visitors here, and we have 124 listed on our database. The rental property options that can cater to large groups in this area include:

  • If yours is a crew of 6, we've got 196 vacation homes perfect for that size. Book a night for as little as $350.
  • If you've got 8 in your family, you'll be thrilled to hear that there are 156 vacation homes suitable. You can get one for as little as $219 per night.
  • Organizing a trip away with 7 guests? We offer 28 vacation homes that will be perfect. Prices start from $107 per night.

So don't fear! When you travel with us you'll be able to bring your uncle, your brother and all your pals to Village of Woodstock.

Where are the cheapest rentals in Village of Woodstock?

Say au revoir to sterile, drab hotel chains! Savor the flexibility of staying like a local in an affordable rental instead. Feast your eyes on the amazing options available for you now on Vrbo. South Royalton is a great area to check out if you want to keep your budget under control. Vrbo has 2 rentals, and the average price is an affordable $72 per night. You'll find another 252 Vrbo rentals awaiting you in or around Killington Ski Area. The average price in this area is $193 a night.

Explore destinations around Woodstock

Killington
600 vacation rentals
Ludlow
655 vacation rentals
Hanover
133 vacation rentals
Enfield
62 vacation rentals
Newport
142 vacation rentals
Grantham
92 vacation rentals
Rutland
1,218 vacation rentals
Lebanon
138 vacation rentals
Chester
919 vacation rentals
Weston
925 vacation rentals
Barnard
184 vacation rentals
Cavendish
478 vacation rentals
Plymouth
932 vacation rentals
Norwich
138 vacation rentals
Fairlee
42 vacation rentals
Rochester
148 vacation rentals
Chittenden
474 vacation rentals
Mount Holly
806 vacation rentals
East Dorset
413 vacation rentals
Springfield
165 vacation rentals