Best underrated winter holiday vacation destinations
Skip the crowds and high price tags this winter
Skip the crowded slopes and overbooked resorts this season. Some of the best winter escapes are found in places you might not expect—where you’ll find fewer tourists, lower prices, and plenty of charm. These underrated winter destinations are perfect for cozy getaways, family trips, or even a quiet solo adventure. With vacation rentals in each location, you can enjoy comfort, privacy, and unforgettable experiences.
While popular destinations like Aspen or Miami draw large crowds, these underrated spots offer something different: serene landscapes, authentic local culture, and more space to relax. From snowy mountain towns to quiet coastal retreats, each destination gives you the chance to enjoy winter at your own pace, with less noise, lower prices, and memorable experiences.
While many head here for summer sun, Virginia Beach in winter has its own magic. The Holiday Lights at the Beach drive-through display stretches along the boardwalk, and you can enjoy peaceful walks on uncrowded shores. For nature lovers, First Landing State Park offers winter hikes with fewer visitors.
Hidden gem tip: Locals love grabbing fresh she-crab soup at Waterman’s Surfside Grille after a chilly beach walk — a cozy winter tradition.
Featured home: H20 - 360
This Bavarian-inspired town becomes a storybook scene during the holidays. The Village of Lights festival covers the town in millions of twinkling lights, and sleigh rides through the snow make it unforgettable. Skiers and snowboarders can head to Stevens Pass nearby.
Hidden gem tip: Skip the main beer halls and check out Icicle Brewing Company’s taproom for a quieter evening with small-batch seasonal brews.
Featured home: Luxurious Lake Views
Soak in thermal waters while the winter chill lingers outside. Bathhouse Row is decorated with festive lights, and nearby hiking trails in Hot Springs National Park remain open year-round.
Hidden gem tip: Visit Superior Bathhouse Brewery, the only brewery in the U.S. using thermal spring water in its craft beers.
Featured home: Ledgerwood Point
A gateway to Glacier National Park, Whitefish offers a festive downtown, excellent skiing at Whitefish Mountain Resort, fat tire biking on snowy trails, and horse-drawn sleigh rides. The town’s alpine charm makes it a quieter alternative to bigger resorts. And, if you're lucky, watch for the northern lights on clear nights.
Hidden gem tip: Take a winter hike (or snowshoe) on the Whitefish Trail for breathtaking views locals know rival those in the national park — without the crowds.
Featured home: Whitefish Lake Wonder
Blending Native American culture with ski-town vibes, Taos offers Taos Ski Valley, art galleries, and adobe charm. The town square often hosts holiday events, including luminaria displays. Don’t miss the hidden hot springs in nearby Arroyo Hondo.
Hidden gem tip: Visit the Taos Pueblo (a UNESCO World Heritage Site), where traditional holiday dances are still celebrated — an authentic cultural experience.
Featured home: Pueblo Revival
This coastal gem shines with Southern charm. Holiday boat parades and decorated oaks give it a festive feel. Winter brings mild weather, perfect for biking and exploring historic sites, like the historic St. Simons Island Lighthouse.
Hidden gem tip: Locals head to Gould’s Inlet for peaceful birdwatching — it’s especially active in winter when migratory species arrive.
Featured home: Mosley Cottage
Known for world-class skiing, Breckenridge also delivers quirky holiday traditions. The Race of the Santas kicks off the season, while the Victorian-style downtown glows with lights and decorations.
Hidden gem tip: Take a short drive to the Country Boy Mine for a guided snowshoe tour and a bit of Colorado’s mining history.
Featured home: Modern Mountain Sanctuary
This Central California Coast town hosts the Cambria Christmas Market, with over two million lights and festive stalls. Nearby, the Pacific coastline offers dramatic winter scenery and elephant seal viewing at Piedras Blancas.
Hidden gem tip: Wander the Fiscalini Ranch Preserve — a cliffside trail system locals love for quiet coastal views, especially striking in winter.
Featured home: Wanderlust Cambria Seaside Village
Lake Tahoe sparkles in winter with ski resorts, casinos, and snow-covered trails. Holiday events range from fireworks to cozy lodge celebrations.
Hidden gem tip: Instead of the busy ski slopes, try snowshoeing under the stars at Tahoe Meadows — guided night tours reveal a magical side of the Sierra Nevada.
Featured home: Koyukon Escape
Tucked into Central Oregon’s high desert, Sunriver is a quiet winter escape just 20 minutes from Bend. Families can ski or snowboard at Mt. Bachelor, one of the largest ski areas in the Pacific Northwest, or try cross-country skiing and snowshoeing right from town. After a day in the snow, warm up at the Sunriver Brewing Company or enjoy a stargazing session — the area is a certified Dark Sky Place.
Hidden gem tip: Locals know the Sunriver Nature Center & Observatory is open year-round — winter nights are some of the clearest for spotting planets and constellations.
Featured home: Something to Write Home About
No matter where you choose to spend the season, staying in a vacation home gives you the space to relax, celebrate, and feel at home during the holidays. From mountain cabins to coastal cottages, you’ll find the perfect place to make lasting memories.
