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 kitchens. Prices start at $224 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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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.

Activities

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.

Weather

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 2020 property listings offer a large selection of 684 vacation rentals around Woodstock. From 395 house rentals to 82 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:

  • Overlook Mountain Trailhead: 1,032 vacation rentals
  • Woodstock Golf Club: 946 vacation rentals
  • Woodstock Public Library: 981 vacation rentals
  • Karma Triyana Dharmachakra Monastery: 1,031 vacation rentals
  • SweetHeart Gallery: 964 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 395 Houses in Woodstock. Our other popular types of vacation rentals in Woodstock include:

  • Cabins: 82 rentals available
  • Cottages: 82 rentals available
  • Condos/Apartments: 89 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 139 vacation rentals with pool available in Woodstock. Please use our search bar to access the selection of vacation rentals available.

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