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.
What Guests Are Saying About Their Ulster County Stay
“We enjoyed our stay very much! Our family relaxed by the pool everyday. True highlight! Great restaurants nearby especially the Red Onion and downtown Woodstock was artsy, adorable, and fun!”
“This was our second time staying here, and we hope to be back! This place is a beautiful home away from home.”
“We had a wonderful stay. The cabin is so cozy and homey unlike many Airbnbs. The kitchen was well stocked and had everything we needed. It’s not too far from the road but is very quiet. We only saw a couple of cars drive by during our stay. The stairs to the upper bedrooms are very steep and open, but were fine for our group with some extra caution. Highly recommend this place! We are already discussing coming back early next year.”
“Amazing cottage for a perfect getaway out of the city. The house is beautiful and the place very pleasant. Would recommend to anyone who’d like to take some rest and enjoy calm and peace in the middle of the forest. The terrace is great and many hikes are accessible close to the place. Thanks a lot for having us.”
“This is such a great cabin for a weekend getaway! It was so quaint & cozy. The kitchen is full stocked, which was very appreciated, as we cooked most of our meals there. We were sad that the hot tub didn’t meet our expectations because that is a big reason we chose this cabin! Also, the bathtub was not functioning, so there was only 1 shower for 6 people. Management is going to address this so hopefully the second full bathroom will be up and running soon! The location is great.”
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.
Minnewaska State Park Preserve is the anchor, with cliff-top trails, sky lakes, and wide-open views that feel almost surreal for being just two hours from the city. The Sam’s Point Area adds ice caves and high-elevation blueberry barrens to the mix, while Mohonk Preserve offers miles of carriage roads and single-track through some of the best terrain in the Northeast. For a shorter afternoon hike, Overlook Mountain near Woodstock tops out at a fire tower with panoramic Catskill views. Most of our Ulster County homes put you within 20 to 30 minutes of all of it, so a full day on the trails still ends with a proper kitchen and a comfortable place to settle in.
Ulster County’s creative roots run deep. Opus 40 in Saugerties is a monumental outdoor sculpture carved from a former bluestone quarry, and it remains one of the most striking art sites in the state. In Woodstock, the Woodstock Artists Association and Museum keeps the town’s long artistic history feeling current, and live music venues like Levon Helm Studios and Colony Woodstock make it easy to build an evening around a show. Maverick Concerts brings chamber music to the woods each summer. For a deeper cultural afternoon, Dia Beacon, just across the river, is one of the most important contemporary art spaces in the country.
Kingston is the county seat and a genuine destination in its own right: the Stockade District has indie shops, galleries, and some of the best restaurants in the Hudson Valley, while the Rondout Waterfront adds a more relaxed, maritime character. Woodstock needs little introduction, with its walkable village green, galleries, boutiques, and live music on most weekends. Saugerties is quieter and charming, ideal for antiques and a good meal. New Paltz brings a younger energy with its college town cafes, climbing shops, and easy access to the Gunks.
When summer hits, Esopus Creek tubing between Phoenicia and Mount Tremper is a local rite of passage: a mellow float through Catskill scenery with easy put-in spots and outfitters who handle the logistics. Rondout Creek near High Falls is another favorite for a quieter paddle. The Ashokan Reservoir, a key part of NYC’s water supply, offers the Ashokan Rail Trail, an 11.5-mile shared-use path perfect for biking or an easy walk along the water. Several of our properties sit within a short drive of the creek, so you can be on the water before lunch and back on the deck with a cold drink by late afternoon.
Ulster County’s dining scene has matured into something genuinely exciting. In Woodstock, Silvia is the go-to for wood-fired, locally sourced cooking, and Cucina offers contemporary Italian in a warm setting. Kingston’s restaurant row keeps expanding: Restaurant Kinsley, Lola’s Cafe, and the Rondout waterfront spots are all worth planning around. In New Paltz, The Village TeaRoom and Main Course are local favorites. For a different kind of meal, stock up at a farmers’ market or farm stand and cook in your rental kitchen. Every Red Cottage home is set up for it.
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 | 16โ34 | Medium | $$ | Belleayre and Hunter ski days, cozy cabin nights, fireside evenings |
| February | โ๏ธ Coldest stretch, reliable snow | 17โ37 | Medium | $$ | Peak ski weekends, snowshoeing Mohonk Preserve, quiet Woodstock walks |
| March | ๐จ๏ธ Late winter, snow softening | 26โ47 | Low to Medium | $$ | Last ski days, early trail hikes, uncrowded Kingston weekends |
| April | ๐ง๏ธ Cool spring, waterfalls running high | 36โ59 | Low | $ | Shawangunk Ridge hikes, waterfall chasing, shoulder-season deals |
| May | ๐ธ Mild and green, everything waking up | 46โ70 | Medium | $$ | Minnewaska trails in bloom, farmersโ markets open, long lunches in New Paltz |
| June | ๐ค๏ธ Warm early summer, ideal conditions | 55โ78 | High | $$$ | Best all-around weather, Esopus Creek tubing begins, Woodstock live music |
| July | โ๏ธ Hot and peak summer | 60โ83 | Very High | $$$$ | Pool and creek season, Maverick Concerts, farm stand bounty, family trips |
| August | โ๏ธ Warm and sunny, full summer energy | 58โ81 | Very High | $$$$ | Tubing, swimming holes, outdoor dining, Kingston waterfront evenings |
| September | ๐ Pleasant with cooler nights | 50โ74 | High | $$$ | Perfect hiking weather, early foliage, fewer crowds, best balance of energy and ease |
| October | ๐ Crisp and peak foliage | 40โ62 | Very High | $$$$ | Fall color drives, Catskill ridge hikes, harvest festivals, apple orchards |
| November | ๐ง๏ธ Cool, quiet, off-season settling in | 32โ50 | Low | $ | Slow weekends, best availability, gallery browsing, Kingston restaurant scene |
| December | โ๏ธ Cold with early snowfall | 22โ38 | Medium | $$ | Holiday shopping in Woodstock, first ski days at Belleayre, cozy fireside stays |
Frequently Asked Questions
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.
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.
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.
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.
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.