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 $150 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


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.

What are the top vacation rentals in or near Woodstock?

Whatever your vacation needs, you'll find a rental property in or around Woodstock that suits your style. Take a peek at these favorites:

  • Log Cabin Living On The Esopus Creek is a hit with guests. Around 7 miles from Woodstock, it has 2 bedrooms and plenty of handy amenities, including lowered locks and a toaster.
  • 1876 Eyebrow Colonial Home On 36 Acres is another winner, offering 3 bedrooms, a TV, shopping and more. It's around 6 miles from Woodstock.

For even more great options, use the search bar at the top of the page to find the perfect Woodstock vacation rental for you.

What's the best place to stay if you're looking to rent a house for a weekend in or near Woodstock?

With its lovely beaches and family-friendly charm, Pine Hill is a wonderful destination to go for a weekend break. You'll find it just 20 miles to the west of Woodstock. A big drawcard here is the ever-so-stunning Belleayre Beach at Pine Hill Lake, offering pleasant views of natural beauty. Wander along the seaside or just sit back and relax on the white sand.

Are there one-bedroom vacation rentals in or near Woodstock?

Romantic retreats, business trips or adventures all on your own — a single-bedroom vacation property suits a multitude of occasions. One of our options in or near Woodstock is sure to impress:

  • Reserve Room 10 - Twin Gables Of Woodstock for a couple of days. This one-bedroom property comes with off-street parking options and free WiFi and is not far from downtown.
  • Or maybe Wydeclove Artist Retreat is better suited. Another centrally located one-bedroom option, this place comes with coffee and tea making facilities, a microwave oven and more.

Can I find two-bedroom vacation rentals in or near Woodstock?

At Vrbo, we've got rentals in or near Woodstock to suit everyone's needs. Here are a couple of our favorite two-bedroom options to consider:

  • Leading the list is Top Rated Romantic Rustic Luxury+flowing Stream+walk To Town=brook Cottage. This two-bedroom beauty has handy amenities like a fireplace and a smart TV. You can easily explore Woodstock's exciting attractions from this homely base.
  • Beautiful, Tranquil Woodstock Mountain House With Hot Tub And Ping Pong is another lovely two-bedroom escape. It provides a washing machine, a kitchen and much more.

What are the best three-bedroom vacation rentals in or near Woodstock?

If you need a bit more space for the kids (or your tagalong pal), a three-bedroom vacation rental is the way to go. Vrbo can help you find the best options in or near Woodstock, starting with these:

  • It's not hard to see why Peaceful, Stunning Property 3 Min To Woodstock is popular with many travelers. This spacious retreat comes with WiFi and an ice maker and makes vacationing with family and friends a fun experience.
  • Alternatively, check out the relaxing and roomy vacation property that is Tannery Brook Cottage: Terraced Garden With Patio. Settle in with your nearest and dearest and enjoy its many conveniences, such as air conditioning and daily housekeeping services.

Are there vacation rentals with fire pits in or near Woodstock?

If you love the idea of cozying up by a campfire but aren't as excited about the "camp" part, a vacation rental with a fire pit will tick all your boxes. Enjoy the conveniences of home at one of these options in or near Woodstock that come with this sociable perk:

  • Cozy up with your nearest and dearest around the flickering fire at Swim, Sun, Hike, Enjoy Life In A Private Cottage W. A nearby marina and a chef are other amenities you'll have at hand here.
  • Stoke the embers and then take in the tranquil vibe at 1876 Eyebrow Colonial Home On 36 Acres. This cozy abode also comes with a kitchenette and an oven.