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We found 568 vacation rentals — enter your dates for availability
Discover a selection of 500 vacation rentals in Woodstock, NY 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 $119 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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Find the best place to stay — Woodstock
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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
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 26.4 mi (42.4 km) from the city center.
How many vacation rentals are available around Woodstock, NY?
Our 2022 property listings offer a large selection of 568 vacation rentals around Woodstock. From 432 house rentals to 95 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 Houses in Woodstock?
Yes, of course. Vrbo has 432 Houses in Woodstock. Our other popular types of vacation rentals in Woodstock include:
- Cabins: 95 rentals available
- Cottages: 89 rentals available
- Farmhouses: 15 rentals available
But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.
Can I find a vacation rental with pool in Woodstock?
Yes, you can select your preferred vacation rental with pool among our 118 vacation rentals with pool available in Woodstock. Please use our search bar to access the selection of vacation rentals available.