Our Top Five Winter Getaways in Upstate New York: 2017

For some, the cold is as good excuse as any to jet someplace warm, to swap insulated jackets for inflatable pool floats. But when the wind chill drops, we are quickly reminded of all that we love about winter upstate: bright morning walks on secluded roads; leisurely afternoons in front of a crackling fire; snowshoe hikes through white forests; the smell of smoke curling from nearly every chimney. Whether you choose to hibernate or recreate this season, here are our top five places to stay this winter — from a gorgeous creekside house in Shandaken, to a newly designed hotel in Saratoga, to a cozy modern cabin in Bovina. To make the most of your chilly respite, you’ll find recommendations in each location on where to shop, eat, and explore in the nearby area. Happy Winter!

The Roundhouse
Best Places to Stay in Upstate, NY This Winter. andnorth.com
Best Places to Stay in Upstate, NY This Winter. andnorth.com
  • Take refuge from the cold at The Roundhouse, a former textile factory turned posh hotel overlooking the serene falls of Fishkill Creek. Spread across three mid-century modern buildings in the heart of Beacon, the hotel is an inviting base from which to explore the environs of local shops, markets, galleries, and restaurants. If the cold weather deters you from adventuring outside, enjoy dining at The Roundhouse by Terrance Brennan, the hotel’s capacious restaurant featuring a Hudson Valley-inspired menu, while looking out on the falls through floor-to-ceiling windows.
  • Explore the Area
    Shop: Reservoir
    Eat: Kitchen Sink
    Explore: Dia: Beacon
  • Beacon, NY
    67 miles from New York City

    Images by Brian DiFeo, Ethan Harrison, Sarah Tew
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Rivertown Guest House
Best Places to Stay in Upstate, NY This Winter. andnorth.com
Best Places to Stay in Upstate, NY This Winter. andnorth.com
  • If Hudson has been on your getaway list this year, we recommend settling in at Rivertown Guest House, a restored mid-1800s Italianate Victorian home located just two blocks away from the shops and restaurants on Warren Street. Blending historic elegance with classic updates, this popular Airbnb offers two stunning apartments, complete with gourmet kitchens, vibrant yet relaxing living spaces, and bathrooms stocked with organic bath products from our favorite perfumery, 2 Note.
  • Explore the Area
    Shop: 2 Note Perfumery
    Eat: Wm Farmer and Sons
    Explore: Olana: Historic Home of Frederic Church
  • Hudson, NY
    120 miles from New York City

    Images by Rivertown Guest House and Emma Tuccillo
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Flatrock House
Best Places to Stay in Upstate, NY This Winter. andnorth.com
Best Places to Stay in Upstate, NY This Winter. andnorth.com
  • Gather your family and friends for a spree at Flatrock House, a 3,200 square foot Airbnb situated along the Esopus Creek in the hamlet of Shandaken, just a brisk drive from Phoenicia and Woodstock. Built in 1951, this streamside retreat was once a local bar, disco, and casino in the 60s and 70s before it was retrofitted in 2015 by three friends in Brooklyn. Between two spacious bedrooms on the first floor, a master bedroom and smaller bedroom on the second floor, a chef’s kitchen and dining room, and an upstairs TV/game room, Flatrock is the ultimate respite for the winter season.
  • Explore the Area
    Shop: D-Day
    Eat: Phoenicia Diner
    Explore: Belleayre Mountain
  • Shandaken, NY
    126 miles from New York City

    Images by This Is The Place I Was Telling You About
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Brushland’s Owl Nest
Best Places to Stay in Upstate, NY This Winter. andnorth.com
Best Places to Stay in Upstate, NY This Winter. andnorth.com
  • Experience the wonderland that is Bovina with a stay at Brushland’s Owl Nest, a sunny two-bedroom Airbnb cabin surrounded by the woodlands of Bramley Mountain. Spend your days exploring the snow capped scenery of Delaware County before returning home to cook, lounge, and play games by the wood-burning stove. Owned by our friends at Brushland Eating House, no trip to Bovina is complete without a meal at their restaurant, just ten minutes down the mountain.
  • Explore the Area
    Shop: Kabinett & Kammer
    Eat: Brushland Eating House
    Explore: Hobart Book Village
  • Bovina, NY
    151 miles from New York City

    Images by Christian Harder
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The Brentwood Hotel
Best Places to Stay in Upstate, NY This Winter. andnorth.com
Best Places to Stay in Upstate, NY This Winter. andnorth.com
  • Discover the bucolic surroundings of Saratoga with an escape to Brentwood, a 12-room hotel owned and impeccably designed by Brooklyn-based Studio Tack. Set on the grounds of the historic Saratoga Race Course, this former motor lodge warms our heart with equestrian-inspired details, locally made plush beds, and views of the iconic horse track from every room. Sip hand crafted cocktails at the hotel’s sleek bar, the perfect spot to begin your evening before heading out for the night. Located just a five-minute drive from downtown Saratoga makes Brentwood the ideal starting point for an array of winter activities, from exploring the ski trails at Cole’s Woods, to snowboarding and snowshoeing at Saratoga Spa State Park, to unwinding from the holidays at one of the city’s many spas.
  • Explore the Area
    Shop: Putnam Wine
    Eat: Salt and Char
    Explore: Saratoga Mineral Springs and Spa
  • Saratoga Springs, NY
    189 miles from New York City

    Images by Read McKendree
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