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Vacation Rentals in Ulster County, NY

Explore Red Cottage’s collection of Ulster County vacation rentals, set in one of the most rewarding stretches of the Hudson Valley and the Catskills. From the dramatic cliff trails of the Shawangunk Ridge to the creative energy of Woodstock, the walkable waterfront of Kingston, and the college-town charm of New Paltz, Ulster County puts you right in the middle of it all without ever feeling crowded.

Whether your weekend is built around a ridge hike with big views, a tasting trail through local cideries and breweries, or a slow afternoon browsing shops and galleries in one of the county’s small towns, Ulster County delivers the kind of getaway where every day feels unhurried and full. Our homes here are designed for exactly that: settling in, slowing down, and having a real place to come back to at the end of the day.

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What Guests Are Saying About Their Ulster County Stay

    Discover Ulster County

    Ulster County stretches from the Hudson River west into the heart of the Catskills, covering a landscape that ranges from dramatic ridgelines and deep forest to charming river towns and a genuinely impressive food scene. Whether you are here for a weekend reset or a full week of exploring, the county rewards you at every turn.

      Ulster County Through the Seasons

      Ulster County has something to offer every month of the year, and each month brings a different kind of getaway. Use the guide below to compare typical weather, crowds, and rates so you can plan the perfect visit, whether you are after a winter ski escape, a summer creek day, a fall foliage drive through the Catskills, or a quiet spring hike before the season picks up.

      Month Typical Weather Avg Temp (ยฐF) Crowd Level Nightly Rates Best For…
      January โ„๏ธ Cold and snowy, prime ski season 16โ€“34 Medium $$ Belleayre and Hunter ski days, cozy cabin nights, fireside evenings
      February โ„๏ธ Coldest stretch, reliable snow 17โ€“37 Medium $$ Peak ski weekends, snowshoeing Mohonk Preserve, quiet Woodstock walks
      March ๐ŸŒจ๏ธ Late winter, snow softening 26โ€“47 Low to Medium $$ Last ski days, early trail hikes, uncrowded Kingston weekends
      April ๐ŸŒง๏ธ Cool spring, waterfalls running high 36โ€“59 Low $ Shawangunk Ridge hikes, waterfall chasing, shoulder-season deals
      May ๐ŸŒธ Mild and green, everything waking up 46โ€“70 Medium $$ Minnewaska trails in bloom, farmersโ€™ markets open, long lunches in New Paltz
      June ๐ŸŒค๏ธ Warm early summer, ideal conditions 55โ€“78 High $$$ Best all-around weather, Esopus Creek tubing begins, Woodstock live music
      July โ˜€๏ธ Hot and peak summer 60โ€“83 Very High $$$$ Pool and creek season, Maverick Concerts, farm stand bounty, family trips
      August โ˜€๏ธ Warm and sunny, full summer energy 58โ€“81 Very High $$$$ Tubing, swimming holes, outdoor dining, Kingston waterfront evenings
      September ๐Ÿ Pleasant with cooler nights 50โ€“74 High $$$ Perfect hiking weather, early foliage, fewer crowds, best balance of energy and ease
      October ๐Ÿ Crisp and peak foliage 40โ€“62 Very High $$$$ Fall color drives, Catskill ridge hikes, harvest festivals, apple orchards
      November ๐ŸŒง๏ธ Cool, quiet, off-season settling in 32โ€“50 Low $ Slow weekends, best availability, gallery browsing, Kingston restaurant scene
      December โ„๏ธ Cold with early snowfall 22โ€“38 Medium $$ Holiday shopping in Woodstock, first ski days at Belleayre, cozy fireside stays

      Frequently Asked Questions

      How far is Ulster County from New York City?

      Most of Ulster County is about 1.5 to 2.5 hours from NYC, depending on traffic and where exactly you are headed. Kingston is roughly 1 hour 50 minutes, Woodstock about 2 hours, and New Paltz about 1 hour 30 minutes. It is an easy weekend drive from the city, and most guests are settled in by check-in.

      What are the best outdoor activities in Ulster County?

      Hiking the Shawangunk Ridge (Minnewaska, Mohonk Preserve, Sam’s Point) is world-class and the main draw for outdoor lovers. In summer, Esopus Creek tubing is a local favorite. The Ashokan Rail Trail is great for biking and walking. In winter, Belleayre and Hunter ski areas are a short drive from most of our Catskills vacation rentals.

      Are your Ulster County vacation rentals pet friendly?

      Several of our Ulster County homes welcome well-behaved dogs. The county is excellent for traveling with pets: trails, open spaces, and creek access give dogs plenty to do. Pet-friendly homes are noted in each listing, so check the details or contact us to confirm before booking.

      What is the best time to visit Ulster County?

      It depends on your plans. Fall is peak for foliage, hiking weather, and harvest events. Summer is ideal for creek days, live music, and long evenings outdoors. Winter brings skiing at Belleayre and cozy fireside weekends. Spring is quieter, with great deals, blooming trails, and fewer crowds.

      Do Red Cottage homes in Ulster County work for groups?

      Yes. Our homes are designed for gathering, with spacious kitchens, dining areas, and comfortable living spaces. Many include fire pits, hot tubs, or pool access. For the best fit, look for listings with multiple bedrooms and common areas that match your group’s size and style.