The twin peaks of Sugarbush have emerged in recent years as the serious downhiller’s New England mountain of choice. The half-century-old resort just spent $10 million overhauling its lodge and base facilities, and more than 2,600 vertical feet of challenging runs across 111 trails means there’s rarely overcrowding. Ride on the East Coast’s first ski snowcat ($75; 800-537-8427), an all-terrain vehicle that transports skiers in a cabin with plush seats and a flat-screen TV up to fresh powder areas for crowd-free sunrise or full-moon ski sessions. Even further off the beaten path, spot wild moose and deer on a guided snowshoe trek through backwoods areas. Afterward, drive to the nearby village of Warren, where the Pitcher Inn (pitcherinn.com) serves pan-roasted quail and local burrata in an 1850s white clapboard family estate.
Where to Stay
Minutes from the mountains, sleep in architect David Sellers’s “Archie Bunker,” a high-concept concrete manse filled with vintage artifacts pulled from the nearby Madsonian Museum of Industrial Design. Take the curling set out for a spin on the property’s frozen pond (from $500; airbnb.com/rooms/50102).
Bring the whole crew to a woodsy A-frame house that sleeps ten and includes creative details like a three-story sunlit atrium and a tree-trunk-lined hallway(from $700; airbnb.com/rooms/40651).
Sugarbush’s newest on-mountain lodging option is Clay Brook, where spacious suites include access to outdoor hot tubs and an on-site ski and snowboard valet (from $195; sugarbush.com/clay-brook).
Belying its reputation as a laid-back, weed-legalizing ski-bum town, Breckenridge is hard-core at heart, with some of the Rockies’ highest lift-serviced terrain—at 12,998 tundralike feet—filled with crowd-free bowls and chutes. The cowboy-rogue in the glitzy Vail Resorts family, Breck celebrates its 50th ski year this winter with deals including half-off lodging through December 15 (lift tickets from $67; breckenridge.com). Last season’s renovations at the base of Peak 8, home to an alpine roller coaster and the sixteen-beer-equipped T-Bar (oneskihillplace.com), created an on-mountain hub for all ages. Cruise the Four O’Clock run back downtown, then head to Breckenridge Distillery, which recently opened a bourbon-tasting room offering free samples (breckenridgedistillery.com). Sop up your hooch with western comfort staples (venison stew, buffalo burgers) at Twist (twistbreck.com) before heading back to your hot tub.
Where to Stay
Grab up to fifteen buddies and rent the new-to-market, four-bedroom Glenwild Mountain Home (left) at the Peak 8 base, with four fireplaces, a seven-seat movie-screening room wired for streaming, a six-seater hot tub on the patio, and saucers for scofflaw sledding after dark (from $895; homeaway.com).
The Bear in the Pines, a centrally located four-bedroom Victorian, lets you walk everywhere, from mountain gondola to townie bars(from $460; flipkey.com).
The One Ski Hill resort furnishes rooms with generous kitchens, gas fireplaces, and spa-inspired bathrooms, while offering communal access to a huge slope-side hot tub, two indoor pools, and a private two-lane bowling alley (from $380; oneskihillplace.com).
North Fork, Long Island
The wind whipping off the Sound might make you wonder why you’re vacationing in Long Island in the dead of winter, but the locally grown comestibles won’t. Launch your foraging by sampling a trio of fruit-infused liquors, the latest in the potato-based portfolio at LiV vodka distillery in Baiting Hollow (lispirits.com). Try former White House sous-chef (and current North Fork farmer) Keith Luce’s pulled-pork-and-pork-belly steamed dumplings with homemade barbecue sauce, made with beer brewed in Greenport, at Luce & Hawkins inside the Jedediah Hawkins Inn in Jamesport (jedediahhawkinsinn.com). Take back a bit of Long Island’s bounty at the new Love Lane Market (lovelanemarket.com) in Mattituck, a 3,000-square-foot pantry that lets you stock your rental house with beef from Cutchogue’s new McCall ranch, rotisserie-cooked ducks from Crescent farm, wild arugula from Satur Farms, and honey from Promised Land, among other local delicacies.
Where to Stay
A rustic-modern, three-bedroom converted barn in Southold comes with Wi-Fi, fire pit, koi pond, and bicycles (from $450; airbnb.com/rooms/137256).
Rent one of four modern rooms in an art-filled converted Jamesport potato barn with a fireplace and Zen gardens (from $210; airbnb.com/rooms/228442).
For a quintessential country-inn experience, book one of four serene rooms at North Fork Table & Inn, where chef Gerry Hayden is adding grass-fed beef from McCall ranch to the winter menu (from $200; northforktableandinn.com).
Valle d’Aosta, Italy
Mountain scenery doesn’t get much more spectacular than in Italy’s Valle d’Aosta, an under-the-radar Alps-flanked region tucked between France, Switzerland, and Piedmont, Italy. For serious altitude, beeline to Breuil-Cervinia, which shares the Matterhorn with Switzerland’s Zermatt. Its slopes are some of Europe’s longest and highest, reaching up to 12,740 feet. At Courmayeur, a resort just over Mont Blanc from France’s Chamonix, more than 60 miles of runs come with one of the valley’s liveliest après-ski scenes. Unwind under Mont Blanc in the thermal baths of Pré-Saint-Didier and Saint Vincent, or tuck in to a six-course, home-cooked dinner at the Agriturismo Famille (agriturismolafamille.it). And don’t miss the stunning ruins at the region’s hub, Aosta, namely a spectacular 70-foot-tall section of a first-century Roman theater.
Where to Stay
Sleep eight at an apartment with a Matterhorn view, rain-style shower, and—best of all—a door directly onto the slopes (from $620 per week; homeaway.com/vacation-rental/p839711).
Up to a dozen adults can squeeze into a four-bedroom stone house in the tiny village of Antey-Saint-André, a five-minute drive from the slopes of Chamois or a fifteen-minute drive from Cervinia (from $1,370 per week; casacapoluogo.it).
The Au Coeur Des Neiges resort (above, right) beneath Mont Blanc lets you choose between homey room and stand-alone chalet, along with an anything but rustic spa, ski room (with boot heaters!), and in-house bistro (from $137; aucoeurdesneiges.com).