Woodstock, NY, USA

We found 963 vacation rentals — enter your dates for availability

Woodstock, NY, USA

Woodstock vacation rentals

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.

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.

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.

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.