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.
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.
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.
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.
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.
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.”
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!
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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