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 swimming pools and WiFi. Prices start at $170 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.
Top rated rentals — Woodstock
Destination guide

Enjoy the natural beauty of a Woodstock house for rent

This mountain town shares the name with an iconic music festival, and still embraces the peaceful bohemian atmosphere. Innovative live music performed at Bearsville Theater and Levon Helm Studios keeps the festival's spirit alive. Throughout the area, you can stop in boutique shops selling tie-dye T-shirts and New Age jewelry. The Elena Zang Gallery and several others around town showcase the works of local artists. As with all rental houses in the Catskills, Woodstock's lodgings accentuate the area's natural beauty. The vaulted ceilings and tall windows allow the sunlight in and give you a view of the outdoors

Things to do

See why Woodstock has attracted artists for decades

Woodstock vacation rentals are located near to all the main attractions. A visit to Opus 40 is a must. This incredible sculpture park covers 6.5 acres and most remarkably of all, was constructed by a single man—Harvey Fite—over a period of 37 years. Woodstock is home to many wonderful galleries. Elena Zang Gallery is set in beautiful gardens dotted with sculptures, and exhibits artwork from the most acclaimed artists of the area. There’s also the Center for Photography, which puts on fantastic photography exhibitions, and hosts a large permanent collection.


Adventure abounds in Woodstock

The Catskill Mountains provide a wealth of hiking trails to explore, whether you prefer to take a gentle saunter or to tackle something more challenging. The trail up to Kaaterskill Falls is one of the easiest, but the 1.7-mile-long round trip takes you past spectacular falls—the highest 2-step waterfall in the state. Head up to Hunter Mountain for an exciting day out. In the winter, you can enjoy skiing and snowboarding across 58 trails, and during the summer you can enjoy an adrenaline-pumping zipline adventure, or traverse the hills in a thrilling 4x4 tour.


Woodstock—a year-round destination

If you want to take advantage of the nearby skiing and snowboarding, Woodstock vacation rentals are perfect in winter, when temperatures drop to as low as 13 degrees and the area experiences the most snowfall. If you prefer to explore the great outdoors in warmer weather, June through August is one of the best times to visit, with temperatures of around 65-70 degrees. The shoulder seasons also provide pleasant conditions for enjoying the outdoor pursuits on offer. May through September enjoy mild conditions, with the mercury hovering around the 60-degree mark.

Natural features

Awe-inspiring vistas await in Woodstock

You never have to stray far from Woodstock vacation rentals to enjoy the wealth of hiking provided by the Catskill Mountains. Gorgeous areas like Bluestone Wild Forest and Indian Head Wilderness are home to fantastic trails and bouldering, and also boast breathtaking falls—the sight of which will make even the most challenging hike well worth the effort. Water lovers will enjoy the area, too. The Ashokan Reservoir and Hudson River are both close by, and there are also numerous watering holes for swimming, such as the picturesque Millstream.

How to get there

How to get to and around Woodstock

The nearest airport is in Hudson, NY (HCC-Columbia County), located 27.2 mi (43.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Albany, NY (ALB-Albany Intl.), which is 51.1 mi (82.3 km) away.

How many vacation rentals are available around Woodstock?

Our 2021 property listings offer a large selection of 672 vacation rentals around Woodstock. From 493 house rentals to 99 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.