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 $125 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

Things to do

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 (12.4 mi / 19.9 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (10.8 mi / 17.3 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 Music Shop (0.1 mi / 0.1 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.

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 in or around Woodstock that suits your style. Here are some of our favorites:

  • Take advantage of conveniences like a hair dryer and a blender at "Legendary Big Pink In Saugerties". Located around 4 miles from Woodstock, this property has 3 bedrooms and good guest reviews.
  • Another great choice is "Incredible “walkable” Rental With Sawkill Creek Views", which is around 1 mile from Woodstock. Featuring 2 bedrooms, a phone and a washing machine, it has everything you need to make your visit comfortable.

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 are the best tiny house vacation rentals in or near Woodstock?

Punching way above its weight when it comes to character and ingenuity, a tiny house vacation rental in Woodstock puts you on the doorstep of big adventure. Turn off your gadgets and turn your focus to nature at one of these pocket-sized escapes:

  • Take time off and clear your mind at "Breezy Hill Tiny House - Rustic And Cozy Tiny House Getaway". Located in Accord, a separate dining area and heating are just a couple of the amenities included here.
  • "Belleayre Casita De Campo Tiny House" comes with a range of comforts, such as a hair dryer and a garden. Located in Big Indian, you'll be able to live large in this small but well-designed abode.

Can I find log cabins to rent in or near Woodstock?

Select a stunning log cabin from the many dotted in or around Woodstock and you'll soon be inside your timber-clad hideaway, drink in hand, reclining by a crackling fire. But adventure is just outside your front door too. These cabins promise the perfect blend of comfort and fun:

  • "Log Cabin Living On The Esopus Creek": Enjoy a week relaxing and resting at this fantastic vacation home nestled in nature. Once you feel refreshed, enjoy snowmobiling or snowboarding, which are among the fun activities in this area.
  • "Pristine Mountaintop Log Cabin In Pine Forest": Stay in and enjoy the quiet atmosphere or have a go at some of the thrilling activities nearby, including rafting and golf. You can be as active or chill as you like.

What are the top-rated vacation rentals for weekend getaways in or near Woodstock?

If you've been busier than an ant in a picnic basket, you deserve to escape for a couple of glorious days. Leave work early on Friday and head for one of these weekend getaways in or near Woodstock:

  • Whisk yourself away to "Incredible “walkable” Rental With Sawkill Creek Views". Located roughly 1 mile to the southwest of Woodstock, this delightful retreat has all you need for a chilled out stay, including an iron and ironing board and nearby hunting activities.
  • "Hudson Valley, The Gunks - Beautiful Cottage" is another top-rated option to consider. It's around 20 miles to the southwest of Woodstock and features a boat, coffee and tea making facilities and more.

Can I find studio apartments for rent in and around Woodstock?

Studio apartments are a simple yet stylish pick, perfectly suited for traveling sweethearts or solo stays. Spend your days checking out your new surroundings and your nights resting up in your cozy hideaway. These vacation properties in or near Woodstock are sure to please:

  • Enjoy some time out on your own or take a few pals to "Hudson Valley, The Gunks - Beautiful Cottage". You'll have plenty of amenities at your disposal, including a fridge and internet services.
  • "Streamside Cottage Walking Distance To Town Of Woodstock" is another terrific choice, providing all you could want for a heavenly Woodstock getaway. Useful amenities here include heating and off-street parking options.

Can I find short term rentals in or near Woodstock?

Whether you're after a comfy cottage or a house large enough to fit the family, you'll find the perfect place on Vrbo. Squeeze in a quick break at one of these favorite picks in or near Woodstock:

  • Within easy reach of central Woodstock, "Log Cabin Living On The Esopus Creek" welcomes short-term guests. When you're not chilling out in your comfortable digs, get out and explore everything that's around you.
  • Alternatively, book a couple of nights at "1876 Eyebrow Colonial Home On 36 Acres". This centrally located property makes exploring the sights easy.

What are the best romantic weekend getaways in or near Woodstock?

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is a perfect way to spice up your relationship. Whisk your special someone off for a few days at one of these top escapes in or near Woodstock:

  • Sneak off on Friday for a few nights of passion at "Legendary Big Pink In Saugerties". Around 4 miles from Woodstock, it comes with plenty of nice touches, like a fireplace and winery tours.
  • Alternatively, spend a few days sipping wine and canoodling at "Swim, Sun, Hike, Enjoy Life In A Private Cottage W", around 6 miles from Woodstock. Beauty services and winery tours will help ramp up the romance.

What are the best large group vacation rentals in or near Woodstock?

Take a look at these large group vacation rentals in or near Woodstock and don't worry about leaving anyone off your invite list:

  • A range of amenities including a swimming pool and a firepit make "Luxurious, Private Mtn Estate - Close To Woodstock On 15 Acres W Pool And Hot Tub" a top pick. This generous property has 5 bedrooms and sleeps up to 16 people. From Woodstock's center, it's around 6 miles away to the northeast.
  • Nothing takes priority over being with the people you love, and "Hudson Valley Spectacular Space On A Scenic Mountain" is the ideal place to do that. Located around 14 miles to the south of Woodstock, as many as 18 guests can stay in this vacation rental which has 5 bedrooms. A firepit and a fireplace are among the various amenities on offer here.

What are the best houses for rent with a pool in or near Woodstock?

Of all the amenities a vacation rental can offer, a pool promises the most fun. Take a peek at these houses for rent with a pool in or near Woodstock and spend your time splashing about. Just don't forget your inflatable pizza slice:

  • Pack your swim gear and make a booking at "Beautiful, Tranquil Woodstock Mountain House With Hot Tub And Ping Pong". There are plenty of other great amenities here, including a kitchen and cable/satellite TV services.
  • Alternatively, enjoy a more leisurely pace of life at "Fabulous Newly Renovated Family House Near Woodstock Center". Along with an invigorating pool, you'll also have use of a TV and towels.

Not sure what the weather is like in Woodstock? It has a humid continental climate, with average temperatures in summer ranging from 55 ºF to 80 ºF. If you'd like more inspiration on where to stay in this epic destination, use the search bar at the top of the page and adjust the filters to check out our entire selection of Woodstock vacation rentals.

What are the best large family vacation rentals in or near Woodstock?

Whether your perfect escape is up in the hills or on the beach, you'll have a lot more fun if you share it with people you love. Choose one of these large family vacation rentals in or near Woodstock and bring along the whole gang:

  • Get your group under the same roof at "1876 Eyebrow Colonial Home On 36 Acres", which has 3 bedrooms sleeping up to 8 guests. This retreat is around 6 miles to the northwest of Woodstock and comes with amenities such as a garden and a kitchen.
  • "Luxurious, Private Mtn Estate - Close To Woodstock On 15 Acres W Pool And Hot Tub" also offers the space you need to share special moments with loved ones. This property is around 6 miles to the northeast of Woodstock, and accommodates 16 guests in its 5 bedrooms. A living room and coffee and tea making facilities will help keep everyone content and comfortable.

When you're ready to leave the house and explore, there are loads of family-friendly attractions nearby to keep everyone entertained. Vanderbilt Mansion, Pine Hill Community Center and Stony Kill Falls should be at the top of your agenda.