Photo by Marina Timo

Woodstock vacation rentals

We found 713 vacation rentals — enter your dates for availability

Discover a selection of 59 homes, 12 apartments, and other vacation rentals in Woodstock that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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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 and attractions in and around Woodstock

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Woodstock a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (11.1 mi / 17.8 km)
  • Woodstock Music Shop (0.1 mi / 0.1 km)
  • Kaaterskill Falls (10.9 mi / 17.5 km)
  • Mohonk Golf Course (18.1 mi / 29.2 km)
  • Windham Mountain Resort (19.2 mi / 30.9 km)
  • Woodstock Golf Club (0.5 mi / 0.8 km)

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.

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 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.

Frequently asked questions

What is the best area to stay in Woodstock when booking a vacation rental?
Zena is one of the most in-demand neighborhoods to book a vacation property in Woodstock. Spend your break here and enjoy all the privacy and comfort that comes with having an entire place to yourself.
What is the most popular type of vacation rental accommodation in Woodstock?
The most desirable types of vacation rentals in Woodstock are cottages. Searching for something different? Vrbo offers a variety of options to match the needs of our guests, so you’ll see vacation properties in all shapes and sizes. The perfect fit is ready and waiting for you — book yours today.
How much does it cost to rent a vacation rental in Woodstock?
A range of factors influence what you’ll pay for a vacation rental in Woodstock, including the season, type of property and length of stay. Still, all Vrbo homes have one thing in common — incredible value. Just add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Woodstock?
Prices for beach houses in Woodstock can vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and how many guests to see available options and prices. From there you can use the filters to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly vacation rentals in Woodstock?
Pack a squeezy toy and a bone for the pooch in your life because Woodstock has 145 properties that throw out the welcome mat to pets. Let your four-legged buddy get in on the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Woodstock?
Tick the “pool” box in our handy filter tool and choose from 32 houses with private pools in Woodstock on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is your call when your vacation property boasts its own swimming pool.
What are popular rental amenities in Woodstock?
When it comes to rental amenities that people look for in Woodstock, tennis, a water view and a garden rank highest. With Vrbo vacation rentals, there are options to match your style and taste, whether you’re going away with your partner, family members or even pets.
Are there large group vacation rentals in Woodstock?
With 11 vacation rentals that can host 10 guests or more in Woodstock, you don’t have to keep anyone off the invite list. From fun family vacations to events like birthday parties and weddings, Vrbo will help you find a large group rental to suit the occasion.
Are there vacation rentals in Woodstock that welcome kids?
Gather your whole crew for fun-filled adventures in Woodstock at one of our 133 family-friendly vacation rentals. These stays come with amenities that are ideal for getaways with children, like kitchens, multiple bedrooms and swimming pools. Simply click on the “Properties good for families” filter and decide on your favorite.
What are the top attractions for families in Woodstock?
Keeping the kids happy during your Woodstock vacation is a snap with these awesome family-friendly attractions:

  • Overlook Mountain Trailhead
  • Karma Triyana Dharmachakra Monastery
  • Woodstock Public Library

Are there one-bedroom vacation rentals in Woodstock?
There are 45 one-bedroom properties in Woodstock to pick from. A one-bedroom vacation property is a wonderful choice if it’s only you and your partner or if you’re vacationing alone. Throw in more privacy, space and convenience compared to a regular hotel, and you’ve got the makings of a memorable trip.
Can I find two-bedroom vacation rentals in Woodstock?
Woodstock has 36 two-bedroom properties that you can choose from. Enjoy a vacation home with all the privacy and space you want at a fantastic price on Vrbo.
Are there vacation rentals with WiFi in Woodstock?
Woodstock has 79 vacation rentals with WiFi, so you can stay connected while you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with the family to writing and sending emails, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Woodstock?
Woodstock has 126 vacation rentals where you’ll be able to chill out in air-conditioned comfort. To locate a stay on Vrbo that offers this amenity, enter your travel dates and use the filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Woodstock?
The minimum age allowed can differ across properties on Vrbo, so be sure to check the rules of the vacation home in Woodstock you’re considering. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Woodstock for?
The length of time you can rent a vacation rental in Woodstock differs according to the property. Simply enter your selected dates to look at a list of options offering extended stays. With lots of amenities like air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to discover a perfect place to call your home away from home in Woodstock.
Does Vrbo offer discounts for vacation homes in Woodstock?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fabulous deals and discounts on Vrbo. From weekend trips to extended getaways, we’ve got the perfect space for your next Woodstock escape.

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