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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 youโ€™re 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.

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What Our Guests Are Saying About Their Woodstock Stay

    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.

      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 18โ€“32 Medium $$ ๐Ÿ‚ Ski days, snowy walks, fireplace nights
      February โ„๏ธ Cold, peak winter 19โ€“35 Medium $$ ๐Ÿ‚ Winter weekends, hot tub, and cozy dinners
      March ๐ŸŒจ๏ธ Chilly, late winter, mixed days 28โ€“45 Medium $$ ๐Ÿ‚ Quieter ski days, early hikes, galleries
      April ๐ŸŒจ๏ธ Cool spring, brighter days 38โ€“58 Low $ ๐Ÿฅพ Waterfalls, shoulder-season stays, town exploring
      May ๐Ÿƒ Mild, green and fresh 48โ€“68 Medium $$ โ›ฐ๏ธ Hiking, Ashokan Reservoir days
      June ๐ŸŒค๏ธ Warm, early summer 55โ€“75 High $$$ โ›ฐ๏ธ Long days outdoors, concerts, farm-to-table dinners
      July โ˜€๏ธ Warm, peak summer 61โ€“80 Very High $$$$ ๐ŸŠ๐Ÿปโ€โ™€๏ธ Pool time, live music weekends
      August โ˜€๏ธ Warm, peak summer 58โ€“78 Very High $$$$ ๐Ÿฅพ Long weekends, outdoor dining, easy day trips
      September ๐ŸŒจ๏ธ Pleasant, cooler nights 52โ€“70 Medium-High $$$ โ›ฐ๏ธ Best hiking weather, culture, fewer crowds than summer peaks
      October ๐Ÿ Crisp, fall color season 42โ€“59 High $$$ ๐Ÿš— Foliage drives, harvest season, cozy nights out
      November ๐ŸŒจ๏ธ Cool, quiet off-season 32โ€“45 Low $ ๐Ÿก Slow weekends, art and shops, relaxed dining
      December โ„๏ธ Cold, early snow, holiday feel 24โ€“37 Medium $$ ๐ŸŽ„ Holiday escapes, early ski days

      Frequently Asked Questions

      How far is Woodstock, NY from New York City?

      Woodstock is an easy weekend drive from NYC, usually around 2 hours depending on traffic and where your home is located in the area.

      Do I need a car in Woodstock?

      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.

      Is Woodstock a good winter getaway?

      Yes. Woodstock is great for cozy weekends with fireplaces and snowy scenery, plus convenient access to ski areas like Belleayre and Hunter for day trips.

      Are Red Cottage Woodstock rentals pet-friendly?

      Some homes welcome dogs. Pet policies vary by property, so check each listing for whether pets are allowed, any fees, and house guidelines.

      Do any Woodstock rentals have a hot tub, pool, sauna, or gym?

      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.