A cozy weekend getaway is one of the easiest ways to shake off the winter blues. Once the holidays have passed and crowds thin out, small towns across the country settle into a slower, more inviting rhythm. To round up the best places to go, we asked travel advisors and experts to share their personal picks, which span the map—from New England villages and Midwest main streets to Western mountain towns. With fewer crowds, better hotel availability, and plenty to see and do, these destinations are especially well-suited to winter travel. Many offer access to winter sports like skiing or snowboarding, but simpler comforts—good food, walkable downtowns, and an overall slower pace—are often just as compelling.
Lenox, Massachusetts
Miraval Berkshires Resort and Spa
Located in the Berkshires, the town of Lenox is “especially appealing for travelers seeking a wellness-focused winter weekend,” says Fora Travel cofounder and Travel + Leisure A-List advisor Henley Vazquez, noting that the town is home to two World’s Best Award–winning wellness resorts: Miraval Berkshires and Canyon Ranch Lenox. These all-inclusive properties offer everything from guided paddling and cooking demonstrations to sound baths, with plenty of spa treatments rounding out the experience. Outside the resorts, visitors can enjoy hiking and snowshoeing along scenic trails at Pleasant Valley Wildlife Sanctuary, skiing in nearby Jiminy Peak, or exploring Lenox’s quaint downtown dotted with independent shops and restaurants.
Taos, New Mexico
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With a population of under 6,500, Taos feels intimate and unhurried in winter, when snow-capped peaks frame the historic adobe architecture around the central plaza. Best known for its art scene and dramatic high-desert landscapes, the town also serves as a gateway to serious winter adventure, with downhill skiing and snowboarding at nearby Taos Ski Valley. Evenings are low-key, whether that means gallery hopping near the historical Taos Plaza (don’t miss the Taos Artist Collective), savoring hatch chile–spiked New Mexican dishes at spots like La Cueva Café and Michael’s Kitchen, or unwinding at wine bars such as Corner Office and Barra Vino. Just outside town, Taos Pueblo offers a powerful look at living Indigenous culture through its centuries-old adobe architecture. Back downtown, check into the newly opened Hotel Willa, a design-forward stay with an on-site gallery, thoughtfully styled rooms, and a cozy restaurant.
Litchfield, Connecticut
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About 100 miles from Manhattan, this small town is “perfect for a low-key winter weekend,” says Vazquez. She continues, “Snowy country roads, historic homes, and cozy inns give it a timeless New England feel, making it especially appealing for couples or solo travelers looking to slow down.” Days here can be as active or laid-back as you’d like, with nearby trails and slopes for skiing and snowshoeing at White Memorial Conservation Center, Mohawk State Forest, and Mohawk Mountain, as well as scenic drives through Topsmead State Forest. Accommodations-wise, Vazquez is a fan of The Belden House, which she describes as “a new, wonderfully cozy hotel with a lovely spa.”
Highlands, North Carolina
Visit NC
Tucked into the Blue Ridge Mountains, the town of Highlands has a “slower pace and misty mountain views that feel especially romantic in the colder months,” says Vazquez. Set at 4,118 feet within Nantahala National Forest—where North Carolina, South Carolina, and Georgia meet—the town is at one of the highest elevations in the Southeast. Winter highlights include waterfall hikes to Dry Falls, Bridal Veil Falls, and Glen Falls, which remain striking even in freezing temperatures; snow tubing and mountain coaster rides at Highlands Outpost; and skiing at Sapphire Valley Ski Area, less than 15 miles away. When it comes time to rest your head, options abound from the luxe Old Edwards Inn and Spa to the quaint Half-Mile Farm and the rustic Highlander Mountain House & The Ruffed Grouse Tavern.
Crested Butte, Colorado
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“While best known for skiing, Crested Butte retains a true small-town soul, especially in winter,” says Julie Palo Hayes, travel advisor and founder of Ramble & Vine, an affiliate of SmartFlyer. “Its colorful historic downtown, locally owned shops, and relaxed après-ski vibe make it feel welcoming rather than flashy.” Secluded without feeling fully remote, about a four-hour drive from Denver, the mountain town shines brightest in winter, with downhill skiing and snowboarding at Crested Butte Mountain Resort, Nordic skiing on an extensive trail network accessible directly from town, and snowmobiling in the surrounding backcountry. For those who prefer a more laid-back pace, stroll historic Elk Avenue, where colorful Victorian buildings house beloved spots like Camp 4 Coffee, Butte Bagels, The Breadery, and The Secret Stash; alternatively, warm up inside the Crested Butte Museum to learn more about the region’s mining history. With just five suites, the luxe Eleven Scarp Ridge Lodge offers a distinctly intimate stay. Housed in a converted saloon with a striking blue façade, the lodge sits just off Elk Avenue.
Quechee, Vermont
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In eastern Vermont, just outside Woodstock, Quechee offers “the perfect mix of stunning scenery and understated luxury,” says Palo Hayes. “A visit to the Simon Pearce flagship is a must, where travelers can watch glassblowing in action and dine overlooking the Ottauquechee River Falls.” It’s also nearly impossible to be bored here, Palo Hayes adds, noting that the town is ideal for antiquing, Nordic skiing, ice skating, or downhill skiing at nearby Ski Quechee, which is smaller and far less crowded than some of the region’s bigger-name resorts. Outdoor lovers can also explore Quechee State Park, home to year-round wooded trails and scenic overlooks. The historical Quechee Inn at Marshland Farm, initially built in 1793 and now on the National Register of Historic Places, offers cozy accommodations just steps from the village center.
Jackson Hole, Wyoming
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Jackson Hole may be world-famous for its skiing, but it remains surprisingly compact, with a small-town feel—it has just over 10,000 residents— despite its outsized reputation. Vazquez describes it as “magical in winter—rugged, dramatic, and authentically Western,” making it “ideal for travelers who want serious scenery and adventure, but with exceptional luxury lodging to retreat to at the end of the day.” Beyond the slopes, winter musts include wildlife spotting in Grand Teton National Park, a sleigh ride through the National Elk Refuge, and strolling downtown Jackson, known for its iconic antler arches. Come evening, make a beeline for the historic Million Dollar Cowboy Bar for a round of line dancing before turning in at one of the area’s standout luxury stays. Vazquez recommends the Four Seasons Resort and Residences Jackson Hole for skiers, thanks to its ski-in/ski-out access and seamless slope-side service, as well as Caldera House, which she says is “great for groups or longer stays” thanks to its all-suite accommodations.
Hudson, New York
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Just two hours from Manhattan—and easily accessible via Amtrak—Hudson makes an easy weekend escape for travelers short on time. Known for its well-preserved historic architecture, vibrant antiques scene, and excellent farm-to-table dining, the riverfront town offers something for every type of visitor. And while most people arrive in spring, summer, or fall, Palo Hayes notes that “winter brings a quieter pace that allows travelers to fully enjoy the town’s creative energy without the crowds.” It’s also a prime season to score deals at sought-after stays like The Maker. Located in the heart of downtown on Warren Street, the stylish boutique hotel is known for its scene-y restaurant and lounge and cozy-chic accommodations, some with en-suite fireplaces. Hudson also makes an excellent base for exploring the region, with easy access to skiing and snowboarding at Hunter Mountain and Windham Mountain, as well as snowshoeing, cross-country skiing, and cold-weather hikes.
Leavenworth, Washington
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Around two and a half hours from Seattle, Leavenworth is a Bavarian-style village that feels as if it’s been plucked straight from Europe, with alpine architecture and German beer halls. While it’s especially popular during the Christmas season, crowds tend to thin out after the holidays, making winter a smart time to enjoy the town’s snow-dusted charm without the peak-season bustle. Don’t skip town without a visit to the Nutcracker Museum or the Leavenworth Reindeer Farm, and be sure to also carve enough time to embark on scenic strolls through Waterfront Park along the Wenatchee River. Finally, snag a room at the rustic-chic Hotel Leavenworth, which puts you within easy walking distance of Front Street’s shops, restaurants, and beer halls.
Galena, Illinois
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In northwest Illinois, about three hours from Chicago, Galena is a storybook small town known for its exceptionally well-preserved 19th-century architecture and mining history. Its walkable Main Street—lined with independent shops, cozy restaurants, and local wineries like Galena Apothecary, Log Cabin Steakhouse, and Galena Cellars Vineyard & Winery—makes it an especially appealing winter getaway. Cold-weather highlights include downhill skiing and snowboarding at Chestnut Mountain Resort, as well as cross-country skiing, snowshoeing, and ice skating at the Nordic Center at Eagle Ridge Resort, where staying on-site means warming up by a crackling fireplace, indulging in spa treatments, and tucking into comfort fare like giant Bavarian pretzels and crispy cheese curds.
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