Sullivan County Vacation Rentals
Explore Red Cottage’s collection of Sullivan County vacation rental homes, just a scenic drive from New York City and the greater tri-state area. With the rolling ridgelines of the Catskills, the legendary trout streams of the Beaverkill and Willowemoc, and a quietly thriving food and arts scene that surprises every first-time visitor, Sullivan County is a destination made for trading the noise of the city for something that actually restores you.
From fly fishing on world-class rivers and hiking above the treeline to farm-forward restaurants, independent breweries, and evenings around a fire pit with nowhere else to be, Sullivan County holds more than most people expect, and nearly always delivers more than they hoped for.
What Guests Are Saying About Their Sullivan County Stay
“We absolutely loved our stay! Lovely cabin, equipped with absolutely everything, you could imagine! So many games and books, that we were not bored for a second. In my few trips to Catskills, this was by far the best place we have stayed!”
“We had the most wonderful stay! The house is well appointed, cozy, and the location is beautiful. Hot tub was fantastic, especially in the snow! Host was super communicative and welcoming. We would love to return.”
“We had a perfect weekend stay here โ especially loved the stocked kitchen and cozy interiors. Would definitely recommend!”
“This is our third year spending a long weekend in Livingston Manor. The home was perfect size for 4 couples and a toddler with 5 bedrooms and 3 full bathrooms. The house was clean and spacious with great indoor and outdoor space. The firepit area was perfect for an evening fire and smores and the location was convenient to get into town and to local areas like Roscoe and Calicoon. We highly recommend staying here!”
“Our family and dogs had a wonderful time at Brookside Manor! The house was large enough for our group and the property is beautiful. We came to enjoy the fall season and had lots of fun visiting local breweries and Livingston Manor. Highly recommend!”
“We had a truly wonderful stay! We spent most of our time indoors cooking, and the kitchen was absolutely perfectโwell-equipped, spacious, and a joy to use. It made celebrating Thanksgiving especially memorable. The whole place was warm, comfortable, and exactly what we needed for a relaxing holiday getaway. We’d happily stay here again!”
Discover Sullivan County
Sullivan County packs a remarkable range into its quiet Catskill landscape. From the legendary trout rivers of the Beaverkill Valley to the Delaware River’s wide bends and the Bethel Woods concert grounds, it’s a place where the scenery changes with the seasons and there’s always a compelling reason to come back.ย
The Neversink Gorge delivers some of the most dramatic riverside hiking in the county, winding through a deep hemlock-lined canyon. The Basherkill Wildlife Management Area is ideal for gentler walks with exceptional birding. Bear Spring Mountain and the Mongaup Valley trails round out a solid roster for all ability levels.
Sullivan County is the birthplace of American fly fishing. The Beaverkill and Willowemoc rivers are two of the most storied trout streams in the country, and the Catskill Fly Fishing Center and Museum in Livingston Manor tells the full story. The upper Delaware rounds out the county’s world-class fishing with wild trout and smallmouth bass.
Bethel Woods Center for the Arts, built on the original Woodstock festival grounds, hosts major outdoor concerts all summer and runs a genuinely engaging museum year-round. Galleries, artisan studios, and weekend markets in Livingston Manor and Callicoon add plenty of texture for an easy, rewarding afternoon off the trail.
Hops Petunia and The Farmer’s Wife in Livingston Manor are both worth planning a lunch around. The Laundrette is a local favorite for ingredient-driven dinners, and Catskill Brewery is a destination taproom in its own right. Farm stands throughout the county make stocking your rental kitchen just as appealing as going out.
Holiday Mountain Ski and Fun Park in Monticello is Sullivan County’s home mountain: uncrowded, approachable, and genuinely fun for families and beginners. The tubing hill is a crowd-pleaser for kids of any age. When snow covers the Mongaup Valley and Basherkill trails, snowshoeing becomes one of the quietest pleasures the county offers.
Sullivan County Through the Seasons
No matter the season, Sullivan County has a different kind of getaway waiting and each one is worth the trip. Use the guide below to compare typical weather, crowds, and rates so you can plan the perfect visit, whether you’re after a winter ski escape, a summer river week, a fall foliage drive through the Catskills, or a quiet spring retreat before the season picks up.
| Month | Weather Vibe | Avg High / Low (ยฐF) | Crowds | Rates | Best For |
|---|---|---|---|---|---|
| January | โ๏ธ Cold and snowy, prime ski season | 33 / 14 | Medium | $$ | Holiday Mountain skiing and tubing, fireside evenings, cozy Catskill stays |
| February | โ๏ธ Coldest stretch, good snow conditions | 37 / 16 | Medium | $$ | Best ski weekends, snowshoeing the Mongaup Valley, quiet river towns |
| March | ๐จ๏ธ Late winter, snow softening | 47 / 25 | Low to Medium | $$ | Last ski days, early trail walks, uncrowded Livingston Manor weekends |
| April | ๐ง๏ธ Cool spring, rivers running high | 60 / 36 | Low | $ | Trout season opening weekend, Neversink Gorge hikes, peaceful getaways |
| May | ๐ธ Mild and green, everything waking up | 71 / 46 | Low to Medium | $$ | Fly fishing the Beaver Kill, wildflower trails, long lunches in Callicoon |
| June | ๐ค๏ธ Warm early summer, ideal conditions | 79 / 55 | High | $$$ | Best all-around weather, Delaware River floats, Bethel Woods concerts begin |
| July | โ๏ธ Hot and peak summer | 83 / 59 | Very High | $$$$ | River days on the Delaware, kayaking the Bashakill, farm stand season in full swing |
| August | โ๏ธ Warm and sunny, full summer energy | 82 / 58 | Very High | $$$$ | Lake Superior State Park swims, paddling, outdoor dining and late sunsets |
| September | ๐ Pleasant with cooler nights | 74 / 50 | High | $$$ | Perfect hiking temps, early foliage, best balance of energy and ease |
| October | ๐ Crisp and peak foliage | 62 / 39 | Very High | $$$$ | Catskill color drives, Neversink Gorge hikes, apple orchards and harvest festivals |
| November | ๐ง๏ธ Cool, quiet, off season settling in | 50 / 31 | Low | $ | Slow weekends, best availability, calm trails and uncrowded towns |
| December | โ๏ธ Cold with early snowfall | 38 / 20 | Medium | $$ | Holiday markets in Narrowsburg, first ski days at Holiday Mountain, fireside stays |
Frequently Asked Questions
Yes. Several of our Sullivan County homes include private outdoor pools, making them a popular pick for summer stays and group getaways. If a pool is a priority, filter by amenity when browsing or reach out to our team and we’ll point you straight to the right properties. Homes with pools tend to book up quickly in summer, so it’s always worth reserving early.
Several of our properties welcome well-behaved pets, and Sullivan County is genuinely one of the best places to bring a dog. Miles of trails, open fields, and river access make it easy to tire out even the most energetic companions. Pet-friendly homes are noted in each listing. If you’re traveling with a pet, just check the listing details or contact us to confirm before booking.
More than most people expect. Bethel Woods Center for the Arts hosts major outdoor concerts on the original Woodstock grounds all summer long. The Catskill Fly Fishing Center, local farm tours, river outfitters, and a growing calendar of gallery openings and food events keep the county lively year-round. In winter, Holiday Mountain adds skiing and tubing to the mix. A full guide to local entertainment is included in every guest welcome binder.
Sullivan County occupies the southwestern edge of the Catskill region, and it offers a quieter, less trafficked version of the Catskills experience than neighboring Ulster County. The landscape is defined by river valleys, forested ridgelines, working farms, and small towns that have developed genuine character without losing their rural feel. It’s the part of the Catskills that rewards guests who want something real over something polished.
The holiday season in Sullivan County is a genuinely lovely time to visit. Local towns put on festive markets and tree-lighting events, and the county’s farm stands and artisan shops make for excellent Christmas gift shopping. Holiday Mountain opens for skiing and tubing typically in December, and the quiet of a snow-covered Catskill landscape around the holidays is the kind of thing that becomes a family tradition after the first year.