The 7 Best Winter Rentals in Driving Distance of NYC

Ski. Hot tub. Hot toddy. Repeat.

December 18, 2018 9:00 am

This winter, resist the urge to bury yourself in a mountain of blankets to embark on a Netflix binge. Instead, embrace the chill the old-fashioned way — by going Upstate, to the kind of woods Robert Frost famously waxed poetic about.

So keep your woolen socks and snowshoes close at hand, because today we’ve got seven winter-ready weekend rentals within spitting distance of the city. From a farmhouse in wine country to a modernist ski chalet, these humble abodes prove that winter travel isn’t just for beach-blanket bingo.

The Stone Farmhouse (5 images)

For gettin’ outta Dodge with the whole crew: The Stone Farmhouse
Stroudsburg, PA
Basics: 14 guests, 4 bedrooms, 10 beds, 2.5 baths
Notable features: Ready thyself for 3.7 acres of secluded Poconos beauty with views of the Appalachian Mountains. On site there’s a fire pit for some serious S’mores-ing, while a short jaunt away you’ll find family fun like the Kalahari Indoor Water Park, the Big Wheel Roller Skating Center and paintball.

A-Frame (5 images)

Images from Chris Daniele/Airbnb

For embracing your inner hippie: Sustainable Catskills A-Frame
Kerhonkson, NY
Basics: 4 guests, 2 bedrooms, 2 beds, 2 baths
Notable features: This completely off-the-grid solar-powered gem is your ticket to some well-deserved R ’n’ R. Awaiting you: room for two couples (or a small family), a firepit and drum BBQ grill nestled on two acres of private land. No need for an alarm clock either — you’ll be rising old school, to the questionably soothing bugling of roosters.

1740 (5 images)

For chatting fireside well into the night: Historic c. 1740 Farmhouse
Wallkill, NY
Basics: 11 guests, 5 bedrooms, 5 beds, 3 baths
Notable features: A restoration with rustic charm and modern amenities. And a quick ride away from the Farmhouse, you’ll find Mohonk Mountain House and the Shawangunk Wine Trail, with some 14 wineries at your fingertips.

Old Hudson (5 images)

Images of Unit 1, from Martyn Tompson/ThisOldHudson

For max Instagram likes: This Old Hudson
Hudson, NY
Basics: Unit one: 2 bedrooms, 2 beds, 1 bath; Unit two: one bedroom, one bed, one bath
Notable features: This Old Hudson, aptly described by its designers as “Scandinavian meets Upstate,” is a fantastically curated two-unit destination you’ll wish you lived in. Not quite an AirBnb but cozier than a hotel, the getaway feels high-end and highly comfortable simultaneously.

Dutch Barn (6 images)

For feeling like you’re in a home away from home: Renovated Dutch Barn
Ulster Park, NY
Basics: 6 guests, 3 bedrooms, 3 beds, 2 baths
Notable features: You’re setting yourself up on a whopping 50 acres of property with loads of hiking and horses, but also excellent wifi. There are plenty of other modern amenities to boot, like phone-charging stations, media with surround sound, massages upon request, a workout room, small office and something called a “Zen Room.”

Container (5 images)

For finishing the next great American novel: Container Cabin
Saugerties, NY
Basics: 2 guests, 1 bedroom, 1 bed, 1 bath
Notable features: There’s a hot tub, fire pit, writing desk and record player. Writer’s block be damned!

Glass Cabin (5 images)

For the modernist ski bum: Glass Cabin in the Woods
Hillsdale, NJ
Basics: 4 guests, 2 bedrooms, 2 beds, 2 baths
Notable features: Also a good spot for exhibitionists. Four-wheel drive is recommended in the winter months, but the trek will be well worth it: you’ll get a peaceful retreat for resting your weary limbs after a day of hitting the slopes at Catamount Ski Resort, which is just a quick three-minute drive down the way.

Main image from Chris Daniele/Airbnb


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