Escape Upstate to a Winter Rental Retreat

  |  November 13, 2014
hillsdale rental

Cottage in Hillsdale, Columbia County

There are lots of reasons to rent a vacation pad in upstate New York during the wintertime. For starters, sitting by roaring fire watching the snowflakes gently fall can be a transcendent experience. What better place to make that happen than tucked away in the mountains, or nestled into a cozy cabin in the Hudson Valley? There’s also the fact that many rentals that operate year-round drop their rates during the winter, meaning you can get your dreamy getaway at a much more reasonable price than during the high season. The exception, of course, is renting near the ski slopes. Some places available for rent near winter recreation destinations, like Hunter Mountain, actually raise their rates from December to April, so it’s good to shop around. We do. A lot. Even though we’re not going anywhere. We just like to dream about where we’d go if we did, and here’s a handful of rentals we could easily see ourselves bearing out the cold winter chill, far away from it all.

hillsdale rental2

This renovated barn in Hillsdale, Columbia County is set on 10 acres overlooking the Audubon Sanctuary near the Berkshires. If you need cell service, you’ll have it here. Min. 7 night stay. If you book between now and December 18, you can get it for $600/week. After that, it’s a $1000/week until January 8. Accommodates 3  with 2 beds/1bath. VRBO.


taghanic rental

For a modest cabin in the woods, this place is pretty chic. Love the hardwood floors and tons of windows. Located just off the Taconic Parkway 20 minutes from Hudson in Columbia County. Min. 3 night stay. Accommodates 10 guests, 3 bed/2 bath. Winter rate is $300/night weekdays, $350/night weekends, and $2000/week. VRBO.


high falls rental

The High Falls, appropriately named, is just a hop and a skip from the charming Ulster County hamlet of High Falls. The interior is stylish and comfortable, and the rental’s surroundings are pretty as a picture. Min. 2 night stay and accommodates 8 (3 beds/1.5 baths). Standard rates are $200/night and $1300/week. Book on VRBO and look at more pictures here.


andes rental

Oh so many windows and hilly vistas here in this contemporary rental in Andes, Delaware County. It’s private, for sure, but there are loads of cute towns all over this part of the Catskills, including Margaretville, Delhi, and, of course, Andes itself. Pricy but pretty. Min. 2 night stay. Accommodates 6 guests (3 beds/2.5 baths). Standard rate is $580/night or $3650/week. VRBO.


phoenicia rental

Naturally, we have to include a rental close to the slopes. This stream-side cabin is close to Hunter Mountain, Belleayre Ski Center, and the Emerson Spa (some people prefer to enjoy the winter from a massage table, thank you very much) and sleeps 5 guests within its inviting, knotty pine walls. Min. 3 night stay. Rates are $160/night on weekdays and $220/night on weekends Dec. 1-18. VRBO.


craryville rental

Speaking of skiing, the hamlet of Craryville in Columbia County, where the Avalon Cottage is situated, is mere minutes from the Catamount Ski Area on the NY/MA border. Old fashioned home with fireplaces and 10 acres of land. Looks like it might be a monthly rental for $2500 from Jan 4 to March 31, but double check to be sure (the description says its a 1 week min. stay, but the Rates section says otherwise). Accommodates 5. VRBO.

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