Call the Catskills Home This Winter: Long Term Stays & Rentals
Escape to the Catskills, All Winter Long ❄️⛷️
Though it’s been a long and warm autumn, the Catskills region is due for its first snowfall later this week! Ready or not – and despite what the toasty November temps would have you think – winter is on its way.
Year-round outside attractions make Upstate a great spot to hunker down as a seasonal home base. For lovers of ski, Belleayre, Hunter, Plattekill, and Windham come to mind at the very mention of “winter” – while loads of hiking, snowshoe and cross-country ski trails are readily available too. Cultural offerings like art galleries, movie theaters and music venues really come alive during winter, as nighttime fun shifts indoors. And call us a little biased, but at the end of the day, is there anything better than a sauna session or a cocktail by the fire? Doubtful.
If any of the above sounds enticing, or you have your own reasons to head Upstate this season – read on. In today’s Escape Club, we’re sharing a list of some monthly/long-term rentals to get you and yours Upstate this winter. (As always, with pets and family in mind too!)
Take a look, and get booking. Contact info for each is listed below.
- The EB Team
The Leeway in Mt. Tremper, NY
Just over two hours north of NYC, The Leeway is a picturesque, nine-room boutique motel in Mt. Tremper, NY. Set on the banks of the Esopus Creek, the motel offers the perfect blend of modern comfort, midcentury vibes, and natural beauty – and filled with amenities needed for a relaxing Upstate getaway (check out EB’s recent feature on The Leeway for more information).
Located in the Northern Catskills, The Leeway is only twenty minutes from Belleayre Mountain, less than thirty minutes from Hunter Mountain, and just under forty minutes away from Windham Mountain. In addition to its proximity to skiing, the motel is also close to sought-after hiking and snowshoeing trails in the Catskill Park. Before hitting the trails, stop into the Catskills Visitor Center in Mt. Tremper to rent snowshoes, trail crampons, and trekking poles for your adventure.
This winter, The Leeway is opening its rooms to season-long rentals – January 1st through April 1st – starting at just $4,000 a room. Rented rooms will not be shared (meaning this is a very limited-time offer, since The Leeway only has nine of them!) and will be readily available for the entire season. Housekeeping will also visit the room once a week, making sure it’s in good condition for every one of your visits.
Booking inquiries can be sent to stay@the-leeway.com.
Mountaintop Cottage in Livingston Manor, NY
This mountaintop cottage – also a primary residence – rents only during winter while the owner is away. Located in the very cute town of Livingston Manor, its function as a primary residence means this rental is fully equipped with all the comforts of home, plus loads of character.
Features include two bedrooms, totally renovated bathroom and kitchen, cozy living room with a fireplace (firewood included), home gym, office space with a large desk and printer, hot tub with scenic views, and washer/dryer. Its size is perfect for couples and small families, and very ideal for WFH with a dedicated office. Well-behaved, trained furry friends are welcome! (New photos coming soon of 2024 upgraded kitchen and bathroom.)
120 miles from NYC, Shandelee Mountain Oasis is five minutes to Main Street Livingston Manor with excellent dining, multiple bars and breweries, world-class art gallery Catskill Art Space, and an abundance of cute boutique shops. Check out the Escape Brooklyn Guide to Livingston Manor, NY to get inspired.
Pricing is $3,500/month. Dates are flexible, roughly February 1 to May 1, 2025. Prioritizing renters who are willing to commit to longer term stays vs. monthly rentals, but reach out with dates and inquiries.
Inquiries can be sent to shandeleemountaincottage@gmail.com.
Perch Cottages in Boiceville, NY
On the other side of the Catskills, just shy of 100 miles north of NYC, Perch Cottages offers a unique opportunity to rent their popular creekside cottages from January through March. Their proximity to Catskills ski mountains like Hunter, Windham and Belleayre is perfect for snow bunnies (and those who prefer to cozy up in lodges). After a day on the mountain, head back to Perch and warm up in the newly added barrel sauna before enjoying an evening in the cottages.
Three pricing tiers for the different sizes of cottages (with different amenities) are available. Rates start at $7,500 for the entire season or $2,500 a month. Seasonal rates are for the period of January 1 through March 31, 2025.
Falcon Cottage: $7,500 season, or $2,500 monthly
Starling Cottage: $7,875 season, or $3,150 monthly
Cardinal Cottage: $7,875 season, or $3,150 monthly
Eagle House: $10,500 season, or $4,000 monthly
Check out the Escape Brooklyn feature on Perch Cottages to get a feel for the property and the surrounding region.
Inquiries can be sent to hello@perchcottages.com.
Dawson Farmhouse in Kerhonkson, NY
This winter, enjoy an extended stay at Dawson Farmhouse, a classic Upstate retreat tucked at the base of the Catskill Mountains. Set on thirteen wooded acres, this three bedroom, three bathroom home fuses bohemian charm and contemporary farm style, making for a comfortable season-long stay.
Spend winter mornings wrapped in a blanket and enjoying a cup of coffee on the screened-in porch. Then, head outside to snowshoe or cross-country ski through the wooded property. Those looking for Alpine skiing can make the trek to Belleayre Mountain, which is just shy of an hour north of Dawson Farmhouse. Winter hikers can head to the Ashokan Quarry Trail for stunning views of the Catskills, just fifteen minutes from the rental.
After a day enjoying the outdoors, spend the evening warming up in front of Dawson Farmhouse’s grand stone fireplace (or stay outside and gather around the fire pit). Prepare meals in the kitchen, then head to the dining room to eat, drink, and be merry.
This winter, extended stays at Dawson Farmhouse start at $5,000/month, available January through March. For more info, contact hello@managethishome.com.
Modern Farmhouse by the Falls in Kerhonkson, NY
Quiet luxury meets nature’s beauty at Manage This Home’s newest vacation rental in Kerhonkson, NY. Post-holidays, this vacation rental’s calendar is clear, so the owners have decided to rent it for winter.
Start the day admiring views from the treehouse-like covered porch, followed by an afternoon exploring Kerhonkson’s rich landscapes, including forest, waterfalls, and farmland. In the evening, prepare a meal in the gourmet kitchen before getting cozy in the dining room to enjoy a meal overlooking the fireplace.
At night, this home’s fire pit is especially alluring, surrounded by big boulders and with the sounds of the creek and waterfall in the distance. Alternatively, spend your afternoon unwinding in the soaking tub in the home’s spa-like bathroom. Winter season rentals (January - March) begin at $6,000.
Inquiries can be sent to hello@managethishome.com.
Hamptons on Hudson in Minton, NY
Set on the banks of the Hudson River, Hamptons on the Hudson is a classic, Hamptons-inspired retreat in the quiet Hudson Valley town of Milton, NY. While waterside living is often reserved for the summer, this picturesque getaway offers a variety of amenities that make it an ideal winter getaway – including a grand fireplace, outdoor hot tub, covered fire pit, and seven acres of land to snowshoe and hike through.
Should you ever want to leave the property, Milton and the surrounding area are known for their wineries (notably, there are seven wineries within seven miles of each other). Highlights include Nostrano Vineyards, which is just a short drive from Hamptons on Hudson, and Stoutridge Distillery & Winery, where you can enjoy wine or a craft cocktail in the tasting room.
For season-long rentals, Hamptons on Hudson’s pricing starts at $7,000/month. This six-bedroom home can sleep up to ten guests, making it adequately sized for large groups looking to escape to the Hudson Valley this winter.
Inquiries can be sent to hello@managethishome.com.