6 winter weekend escapes to get away from reality



The Kaatskeller’s gorgeous outdoor space may not be functional in the winter, but it’s beautiful to walk through on your way to the hidden bar upstairs. Photo: @thekaatskeller

This winter is shaping up to be almost as depressing as last year. After the total snafu of holiday flights with delays ranging from pandemic to polar vortexes, you may be thinking twice about a winter getaway. Most of your excitement comes from dodging omicron like a soldier on a minefield. Will the return of your favorite shows, Search Party, Ozark, and Euphoria be enough exhilaration to get you through winter? If not, weekend getaways will be more important than ever this winter. Grab your vaccinated, recently rapid-tested, friends and book an Airbnb or hotel lodge for cozy time indoors or snowy activities outdoors to keep you busy enough to forget we’re in year three of a global pandemic. 


Skiing is an outdoor activity that can help you enjoy the cold weather. Photo: Meredith Craig de Pietro

Berkshires cannabis & ski in Great Barrington 

Great Barrington is an adorable town with an adorable downtown filled with top-notch restaurants, two hours and 45 minutes by car. There are plenty of adorable Airbnbs to choose from or book an economical stay at The Briarcliff Motel, a pet-friendly updated roadside motel, located at the foot of Monument Mountain. Take a winter hike up the mountain right from your room or go skiing or tubing at nearby Butternut Mountain, a perfect place for beginners still working on their snowplow. (You can rent your gear and sign up for daily lessons.) After you’ve built up your appetite, chow down at No. 10, a classic steakhouse with inventive cocktails, or any of the other top-notch restaurants in town. Whatever you do, don’t forget to experience one of the many legal cannabis dispensaries that sell everything from delightful chocolates to mellow seltzers.


This cabin in the woods is decked out with all the winter feels. Photo: @antrim.stramside

A cabin for 2 or 20 in Livingston Manor

If your idea of the perfect winter getaway is a cabin in the woods, then a weekend at Antrim Streamside in Livingston Manor  (2.5 hours away) is just what the doctor ordered. Here you can rent a romantic cabin for two or a huge one that fits 20 of your friends comfortably. You can arrange yoga or massage in the privacy of your own cabin, take a winter hike by the stream or just curl up in a Pendleton blanket with hot cocoa. Right now you can take advantage of their winter getaway package which includes a steep discount and a gift bag full of winter products. If you have to venture out, The Kaatskeller is known for its gorgeous yard but also has delicious paper-thin pizzas for dine-in or to take out and an upstairs bar that’s open late. 

Related: Livingston Manor, the small Catskills town that delivers a big weekend escape


At North Branch Inn, they make it easy to get outdoors and build a snowman. Photo: @northbranchinn

A touch of winter Americana in North Branch

Foster Supply Hospitality currently has a lock on all the coolest places to stay in the Western Catskills hamlet of North Branch (2 hours and 45 minutes by car), with six different hotels including Kenoza Hall (which writer Tyler Wetherall visited in 2021) and award-winning The Debruce. If you’re looking for a quaint, casual, but luxuriously comfortable experience, look no further than the North Branch Inn. A teeny tiny town in the middle of nowhere consists of a firehouse and this hotel occupying different buildings across the street from each other. Here you’ll enjoy impeccable historic details, a small library curated by One Grand Books, and an indoor restored bowling alley. Grab snowshoes for a hike around the property, borrow a sled, sit by a wood-burning stove with hot cider, or make a reservation at the hotel restaurant which is having chef pop-ups all winter long. 


If you’re willing to spend the money, Mohonk Mountain House is willing to show you a good time. Photo: Courtesy of Mohonk Mountain House

A luxe weekend in New Paltz

Are you counting down the days until the March 18th release of Downton Abbey: A New Era? If so, you may be willing to spend buckets of money on your own weekend at a castle? Mohonk Mountain House, a two-hour drive north, is not cheap, but it is epic, as all your meals and activities are included in the cost of your stay. And in the winter, there is much to do: swim in the indoor pool, ice skate in the outdoor pavilion, drink hot cocoa in front of a 39-foot stone fireplace, borrow microspike shoes for a winter hike, go for a cross country ski adventure on over 30 miles of trails, snowshoe, snow tube, not to mention a million activities just for the kids. 


If your idea of winter means rejuvenating indoors, then this winter retreat has it all– including a room full of snow. Photo: Courtesy of The Inn at Woodloch

Indulge at a snow spa in the Poconos

Topping my winter bucket list is the newly-opened Snow Room at The Lodge at Woodloch, a Poconos-based hotel three hours away by car. “You won’t find anything like this in the United States,” claims their website. It’s like a more gentle cold plunge, but instead of being dunked in a freezing pool, you’ll hang out in a winter wonderland in flip flops and a robe for health benefits. That’s just one of the many experiences on the menu of the 40,000 square foot spa, not to mention other activities you could try like “Zendoodle” classes or birdwatching tours from over 35 offered each day.  


This out-of-the-way hotel offers hygge vibes in a distraction-free zone. Photo: @urbancowboylodge

Wild Western wonderland in the Catstkills

If your idea of a winter getaway skews more Wild West, then the Urban Cowboy Lodge in Big Indian, a three hours drive upstate, just might fit the bill. It’s a place to get away from it all. For real, there’s no cell phone service. The playful vibe is full of Pendleton blankets, over-the-top rustic details like snowshoe wall sconces, cozy nooks, and blazing fires. Expect to start a snowball fight, steam in the Estonian sauna, or relax by the fire. It’s on 68 acres in the middle of Catskills National Park, so if you can’t relax here, it’s time to find a licensed therapist.

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