Destination guide

Art and nature combined in Woodstock

The first thing that comes to mind for many people when hearing the name Woodstock is the acclaimed music festival, and although it never took place here as originally planned, the town still enjoys its well-earned reputation as a place for the arts. Woodstock vacation rentals will put the town right on your doorstep. Head into town to soak up the small-town charm as you explore the many boutiques selling their handcrafted wares. When you’re ready for adventure, try one of the many fantastic activities on offer, whether it’s taking a bike ride around Cooper Lake or hiking up Overlook Mountain to experience incredible panoramas.

Things to do

See why Woodstock has attracted artists for decades

Woodstock vacation rentals are located near to all the main attractions. A visit to Opus 40 is a must. This incredible sculpture park covers 6.5 acres and most remarkably of all, was constructed by a single man—Harvey Fite—over a period of 37 years. Woodstock is home to many wonderful galleries. Elena Zang Gallery is set in beautiful gardens dotted with sculptures, and exhibits artwork from the most acclaimed artists of the area. There’s also the Center for Photography, which puts on fantastic photography exhibitions, and hosts a large permanent collection.


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. If you can't find a flight that's convenient for your trip, you might consider flying into Albany, NY (ALB-Albany Intl.), which is 51.1 mi (82.3 km) away.

Where to stay around Woodstock?

Our 2019 property listings offer a large selection of 715 vacation rentals near Woodstock. From 405 Houses to 92 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Woodstock for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Woodstock?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Woodstock:

  • Bearsville: 301 vacation rentals
  • Hunter Mountain: 97 vacation rentals
  • Windham Mountain Resort: 522 vacation rentals
  • Rhinebeck Village Business District: 15 vacation rentals
  • Glenford: 18 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Woodstock?

HomeAway offers a large selection of vacation rentals near lovely places in Woodstock. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Karma Triyana Dharmachakra Monastery: 1,051 vacation rentals
  • Overlook Mountain Trailhead: 1,050 vacation rentals
  • Woodstock Public Library: 1,005 vacation rentals
  • SweetHeart Gallery: 992 vacation rentals
  • Woodstock Music Shop: 1,005 vacation rentals

But there are many other points of interest around Woodstock listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Woodstock?

Yes, of course. HomeAway has 405 Houses in Woodstock. Our other popular types of vacation rentals in Woodstock include:

  • Cabins: 92 rentals available
  • Cottages: 92 rentals available
  • Farmhouses: 21 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Woodstock?

Yes, you can select your preferred vacation rental with pool among our 175 vacation rentals with pool available in Woodstock. Please use our search bar to access the selection of vacation rentals available.

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