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Woodstock vacation rentals

We found 748 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 69 homes, 21 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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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 sought-after neighborhoods to book a vacation property in Woodstock. Spend your stay here to enjoy the privacy and comfort that comes with having a place to yourself.

What is the most popular type of vacation rental accommodation in Woodstock?

Apartments are the most popular kind of vacation rental in Woodstock, according to our data. Even if you've got something else in mind, Vrbo has vacation homes in all shapes and sizes. Look through our options to find your ideal match.

How much does it cost to rent a vacation rental in Woodstock?

Property type, season and length of stay are some factors that can affect the price of a vacation home. Simply add your travel dates to find your ideal match. From comfy cottages to expansive luxury villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Woodstock?

Prices for beach houses in Woodstock can differ depending on the type and size of the property and when you're traveling. Just enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use the filters to refine your search results by ratings, amenities and more.

Are there pet-friendly vacation rentals in Woodstock?

Pack a travel bag for the pup in your life because Woodstock has 47 vacation rentals that throw out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.

Can I rent a house with a pool in Woodstock?

Pack your swimwear and swim ring, because there are five houses with a private pool in Woodstock. Make a booking at one of these popular vacation rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find a place to make a splash!

What are popular rental amenities in Woodstock?

The most popular rental amenities people are looking for in Woodstock are a fireplace, a chef and a nearby river. Whether you're hitting the road with your besties, family or even pets, Vrbo vacation rentals include the best amenities for starting a new adventure with the people you love.

Are there large group vacation rentals in Woodstock?

There are 11 vacation homes in Woodstock that can host five or more people. From family trips to special occasions, these stays have enough space to spend time with the people that matter the most.

Are there vacation rentals in Woodstock that welcome kids?

With 45 family-friendly vacation homes to select from in Woodstock, now is a great time to introduce the kids to the joys of travel. Just click on our "Properties good for families" filter to find stays loaded with amenities ideal for vacationing families, such as extra bedrooms, swimming pools, bunk beds and entertainment areas.

What are the top attractions for families in Woodstock?

You'll find lots of cool things to see and do with the family in Woodstock, such as:

  • Overlook Mountain Trailhead
  • Saugerties Village Beach
  • Indian Head Mountain

Are there one-bedroom vacation rentals in Woodstock?

Yes, you'll find 28 one-bedroom properties in Woodstock to choose from. A one-bedroom vacation rental is a superb choice if it's just you and your sweetheart or if you're flying solo. Add in more privacy, convenience and space compared to a hotel, and you're bound to have a getaway to remember.

Can I find two-bedroom vacation rentals in Woodstock?

Woodstock has 11 two-bedroom vacation rentals for you to select from. Book a vacation home with all the privacy and comfort you want at an attractive price on Vrbo.

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