Cabin Fever: Cozy & Kid-Friendly Winter Vacation Rentals

airbnb upstate cabin Airbnb

Whether you head to the Berkshires or spend the weekend in the Catskills, these cozy cabins provide a haven away from it all

The snow just started flying and as they say, “winter is coming,” which means it’s time to make a plan. Whether you want to hit the slopes of a nearby ski area, do the holidays in a deluxe chalet, or spend winter break outside the city, we found cozy cabin rentals where you and the family can escape, recharge, and have fun.


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POCONOS

A Pet-friendly Poconos Chalet

Airbnb

Stylishly appointed with a retro vibe, the “Sedgwick Chalet” has five bedrooms. For $50 you can bring a pet. Note: there’s an open staircase so may not be a fit for families with tiny kids. 

Sleeps: 10
Cost: $306/night
Online: airbnb.com

ULSTER COUNTY

An Ulster County Cottage with a Bonus Community Center

Airbnb

Part of Full Moon Resort in Big Indian, NY, “Birdsong Cottage” comes with use of the community center, where there’s free coffee and tea, controlled campfires with s’mores, and more. You can bring your dog here, too. 

Sleeps: 5
Cost: $176/night
Online: airbnb.com

A Tiny House Near Beacon

Airbnb

Talk about cozy! If you’ve ever wanted to experience tiny house living, here’s a chance! This cute trailer is in Marlboro, New York (about 20 minutes from Beacon, home to the museum Dia: Beacon). Somehow, it’s got a king bed in there and wifi, too! (Not recommended for kids two and under.)

Sleeps: 4
Cost: $237/night
Online: airbnb.com

DUTCHESS COUNTY

An Upscale A Frame

airbnb upstate cabin
Airbnb

Built in 1968 but fully renovated in 2020/21, this deluxe Hudson Vally cabin has four bedrooms and 2 and a half baths. A glass facade lets you take in the winter landscape while keeping cozy watching the many streaming services or playing a game from the resident library. When you’re up for an activity, hit one of the ski resorts in the area like Catamount or Butternut, both less than an hour away. 

Sleeps: 7
Cost: $490/night
Online: airbnb.com

COLUMBIA COUNTY

A Chic House in Hudson

Airbnb

Make yourself at home in this two-floor house with a double-sided fireplace, clawfoot tub and rain shower, lots of puzzles and games, and even a deck and fire pit. 

Sleeps: 4
Cost: $264/night
Online: airbnb.com

THE CATSKILLS

A Loaded Ski Lodge Near Hunter Mountain & Phoenicia

Airbnb

In addition to four bedrooms, two bathrooms and two fireplaces (!), this modern ski retreat offers speedy wifi, a record player, toys and games for the kids and amazing views. 

Sleeps: 8
Cost: $450/night
Online: airbnb.com

A Small Cottage For Bargain Hunters

Airbnb

It’s petite, but so is the price. (One of the beds is a sofa bed.) Located in the Catskills, near Woodstock, New Paltz, and a short drive to Hunter Mountain. 

Sleeps: 3
Cost: $112/night
Online: airbnb.com

A Funky Carriage House Near Belleayre

Airbnb

Just a few minutes from the slopes this carriage house is on the site of a Methodist church from 1860. It sleeps six, has quirky decor touches, and a cozy wood stove. 

Sleeps: 6
Cost: $157/night
Online: airbnb.com

THE ADIRONDACKS

A Stylish Cabin Near Lake Placid

Airbnb

Head north for serious skiing and recharge in this modern cabin. Sleeps four comfortably (thanks to double bed bunks) and has a fire pit for apres ski hot chocolate. 

Sleeps: 4
Cost: $210/night
Online: airbnb.com

THE BERKSHIRES 

A Huge Berkshires Log Cabin with Hot a Tub

Airbnb

This sprawling “cabin” with tons of wood, a fireplace, and a hot tub can sleep nine. It’s near ski areas like Catamount and Butternut, as well as Great Barrington, Lenox and the Appalachian Trail.  

Sleeps: 9
Cost: $355/night
Online: airbnb.com

FINGER LAKES

For a 19th Century Schoolhouse with Your Own Private Igloo

Airbnb

Situated in Finger Lakes wine country near Seneca Lake, this schoolhouse has a renovated, modern interior and a heated igloo for morning coffee or nighttime star-gazing. 

Sleeps: 4
Cost: $215/night
Online: airbnb.com

LONG ISLAND

A Chic Off-Season Escape

Airbnb

Yes, there is a lot of white in this former fisherman’s cottage in Port Jefferson, but kids are welcome (and will likely enjoy the cozy bunk beds.) Chill out and enjoy the fireplace, deck, and motorized projector screen for movie nights. It sleeps six.

Sleeps: 6
Cost: $389/night
Online: airbnb.com

Please note, prices listed were valid at the time of publication but rates can fluctuate at different times of the year. If you buy something from the links in this article, we may earn affiliate commission or compensation.

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