Vacation and Cabin Rentals in Woodstock, NY
Tucked into the heart of the Catskills, Woodstock is a mountain town where creativity, nature, and small-town charm come together. With our vacation and cabin rentals, we make it easy to slow down, unplug, and enjoy a getaway surrounded by forested beauty, charming local shops, and a vibrant arts scene.
Whether youโre looking for a cozy cabin retreat, a modern home near town, or a peaceful escape tucked into the woods, Woodstock offers the perfect setting for a memorable stay. Our homes and cabins also feature high-end amenities to make your getaway even more relaxing, from private hot tubs to swimming pools, saunas, and even on-site gyms, depending on the home you choose.
Spend your days exploring scenic hiking trails, browsing galleries and boutiques, or enjoying live music and farm-to-table dining just minutes away. Each season brings its own magic, from colorful fall foliage to quiet winter weekends and sunny summer afternoons outdoors.
Browse below to find your perfect getaway with Red Cottage in Woodstock, NY.
What Our Guests Are Saying About Their Woodstock Stay
“We had an absolutely wonderful stay as a family of three. The home is beautiful, comfortable, impeccably clean, and peacefully set in the woods. The hosts were fabulous โ responsive when we needed things. We canโt wait to return!”
“My fiancรฉ and I, along with our goldendoodle, had a lovely stay at Red Cottage. The house was in a perfect location for us, as it was central to several towns and surrounded by breathtaking fall foliage. We were very cozy and felt right at home. Red Cottage responded very promptly and was so helpful.”
“The cottage was beautiful and spacious enough for our family to relax and enjoy the wonderful winter scenery all around us. We particularly loved the windowed view of the yard where we watched our children play in the snow as we sipped hot cocoa on the couches and listened to music. Very accessible to Phoenicia and the surrounding areaโenjoyed every minute of it!”
“Incredibly charming house in a beautiful area. Everything about our stay went smoothly. Highly recommended!”
“This was a wonderful getaway retreat house! The sauna is lovely, the views of the mountains are great, and the horses in the neighborhood are saying hi. It is SO unique and fun inside. Very warm and nice to have two wood stoves on two levels. We had a great time! Lots of places to have family game time!”
โWe enjoyed our stay very much! Our family relaxed by the pool every day. True highlight! Great restaurants nearby, especially the Red Onion, and downtown Woodstock was artsy, adorable, and fun!โ
Explore Woodstock
Woodstock is a Catskills mountain town where nature and culture come together in an easy, walkable setting. Spend your days between scenic trails, live music, and galleries, then slow down with great meals and small-town browsing in the village center. Whether you are here for a quiet reset in the woods or a weekend built around shops, shows, and dining, Woodstock makes it simple to settle in and enjoy the pace.
For a quick reset, spend time at the Ashokan Reservoir, a key part of NYCโs water system and a source of about 40% of the cityโs daily drinking water in non-drought periods. Pair it with the Ashokan Rail Trail, an 11.5-mile shared-use path along the reservoir from West Hurley to Boiceville, perfect for walking, biking, or winter snowshoeing.
Woodstockโs creative reputation is long-standing, with a strong Arts and Crafts legacy rooted in the area. Byrdcliffe Arts Colony, with construction beginning in 1902, helped shape that history, and WAAM, founded in 1919, continues it with exhibitions and a deep connection to the local art community.
Woodstock is a great base for short, scenic drives to nearby towns. Spend a few hours in Saugerties for Opus 40, a monumental sculpture site set in a former bluestone quarry, or head to Kingston for waterfront walks and a deeper lineup of restaurants and shops.
Woodstock is ideal for ski weekends because the day can be active, and the evening can still feel slow. Ski Belleayre or Hunter, then return to your Red Cottage home for fireplace time and a warm, unhurried dinner. Select homes also include hot tubs, which makes the post-ski wind-down feel like part of the plan.
Woodstock Through The Seasons
Woodstock offers something magical in every season. Whether you’re drawn to vibrant fall foliage, cozy winter snowfalls perfect for skiing, blooming spring trails, or sunny summer days by the creek, each season brings its own charm to this iconic town.
| Month | Typical Weather | Avg Temp (ยฐF) | Crowd Level | Nightly Rates | Best For… |
|---|---|---|---|---|---|
| January | โ๏ธ Cold, snowy, quiet winter | 18โ32 | Medium | $$ | ๐ Ski days, snowy walks, fireplace nights |
| February | โ๏ธ Cold, peak winter | 19โ35 | Medium | $$ | ๐ Winter weekends, hot tub, and cozy dinners |
| March | ๐จ๏ธ Chilly, late winter, mixed days | 28โ45 | Medium | $$ | ๐ Quieter ski days, early hikes, galleries |
| April | ๐จ๏ธ Cool spring, brighter days | 38โ58 | Low | $ | ๐ฅพ Waterfalls, shoulder-season stays, town exploring |
| May | ๐ Mild, green and fresh | 48โ68 | Medium | $$ | โฐ๏ธ Hiking, Ashokan Reservoir days |
| June | ๐ค๏ธ Warm, early summer | 55โ75 | High | $$$ | โฐ๏ธ Long days outdoors, concerts, farm-to-table dinners |
| July | โ๏ธ Warm, peak summer | 61โ80 | Very High | $$$$ | ๐๐ปโโ๏ธ Pool time, live music weekends |
| August | โ๏ธ Warm, peak summer | 58โ78 | Very High | $$$$ | ๐ฅพ Long weekends, outdoor dining, easy day trips |
| September | ๐จ๏ธ Pleasant, cooler nights | 52โ70 | Medium-High | $$$ | โฐ๏ธ Best hiking weather, culture, fewer crowds than summer peaks |
| October | ๐ Crisp, fall color season | 42โ59 | High | $$$ | ๐ Foliage drives, harvest season, cozy nights out |
| November | ๐จ๏ธ Cool, quiet off-season | 32โ45 | Low | $ | ๐ก Slow weekends, art and shops, relaxed dining |
| December | โ๏ธ Cold, early snow, holiday feel | 24โ37 | Medium | $$ | ๐ Holiday escapes, early ski days |
Frequently Asked Questions
Woodstock is an easy weekend drive from NYC, usually around 2 hours depending on traffic and where your home is located in the area.
Yes, we highly recommend having a car for exploring Woodstock. The town center is walkable once you are there, but most hikes, reservoir access, and day trips are easiest by car.
Some homes welcome dogs. Pet policies vary by property, so check each listing for whether pets are allowed, any fees, and house guidelines.
Yes, select Red Cottage homes offer amenities like hot tubs, pools, saunas, and fitness features. Review the individual listing to confirm exactly what is included and any seasonal notes.