Best places to buy a winter vacation home 2019–2020

Killington ranked number two on our 2019 Best Places to Buy a Vacation Home report, so it’s no surprise that the snowy mountain town topped our list focused on winter vacation homes. Travelers flock to Killington in the winter months to take on one of six peaks boasting downhill trails to test every level of skier. Scenic gondola tours lead you to the top of Killington Peak, and sleigh rides through Killington trails are a popular activity December through March. Killington boasts a solid cap rate of 8.31%, and with home prices hovering just above $200,000 buyers and investors can feel comfortable they’ll get the most bang for their vacation rental buck.

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Big Sky is located in southwest Montana, about 44 miles from the college town of Bozeman and 51 miles from West Yellowstone, a popular tourist town and the closest access point to Yellowstone National Park. Though the town’s year-round population is a mere 2,500 residents, visitors from all over the nation book Big Sky vacation homes to enjoy the great outdoors. Big Sky Resort actually consists of two resort areas that share one mountain. These two resorts come together to create “the Biggest Skiing in America”—for every skier or rider, there are at least two acres of terrain. In addition, Big Sky Resort has some of the best snowfall in the Rockies (over 400 inches annually), and some of the shortest lift lines to boot. Cabins and homes in Big Sky, regardless of size, are well booked throughout the year and collectively yield a cap rate of 6.1%.

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The small city of Breckenridge covers under five square miles, yet it boasts a wide variety of indoor and outdoor attractions. With over 70 restaurants and bars, two Nordic Centers, a golf course, 16 museums and galleries, and the Riverwalk Center Outdoor Amphitheater, this town has just about everything visitors could want. Similar to the well-known town of Vail and the ski town of Beaver Creek, Breckenridge comes alive in the winter. With cold-weather activities like dog sledding, sleigh rides, snowmobiling, and even hot air balloon rides over the majestic winter scenery, guests will find that Breckenridge lives up to its winter reputation. The median cost of Breckenridge homes is on the higher end of destinations in our top 10, but both homeowners and guests will find a Breckenridge vacation rental well worth it.

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The “Mountain Lakestyle” town of Dillon lies about 32 miles east of the skiing paradise of Vail, where individuals and groups alike head to relax and take part in winter sports. The cold and snow doesn’t slow Dillon down at all—in fact, it draws in visitors by the thousands. Dillon vacation homes offer access to four of Summit County’s best ski areas: Arapahoe Basin, Keystone Resort, Copper Mountain Resort, and Breckenridge Ski Resort. While Nordic skiers and snowshoers will have their fun on the mountain, trails reserved for hikers and bikers in the summer turn into snowy trails for all winter athletes to enjoy. For a truly magical (and Instagrammable) experience, guests can visit the Dillon Ice Castles, where a display of LED lights illuminates 25 million pounds of ice. Dillon’s median home price of $400,000 sits a bit lower than Breckenridge’s, making it a more affordable option for buyers.

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A popular ski resort destination, Ludlow is home to the family-friendly Okemo Mountain Resort and the perfect place for a relaxing escape from everyday life. Known as “the big Vermont ski mountain that gets the little things right,” Ludlow offers diverse trails that will delight both novices and pros, exceptional snow, and plenty of family-friendly fun. With 667 acres of skiable area and 121 runs, there’s truly something for everyone on the mountain. While Ludlow sees a peak in guests throughout the winter months, it’s truly a four-season destination for travelers—they can check out historical monuments and hiking trails in the spring and summer, and take in the views of changing leaves in the fall. Ludlow homes see a cap rate of around 4.83%.

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Located between Zig Zag and Government Camp, Rhododendron is a charming small town in the Cascade Mountains. Rhododendron is near five different ski resorts—Cooper Spur, Skibowl, Mount Hood Meadows, Summit Ski Area, and Timberline—making it an ideal destination for winter sports. It’s also close to a variety of hiking trails great for taking in views of mountain lakes via snowshoe. Homes in Rhododendron range from cozy, classic A-frames to multi-bedroom homes with large outdoor spaces, but either way a hot tub is always a plus when travelers return home from winter activities. Buyers considering Rhododendron can bank on a typical home cost of around $300,000.

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With beautiful rolling hills and world-class ski slopes nearby, Warren vacation homes offer picturesque views and action-packed outdoor recreation. Encompassing Sugarbush Resort—one of the largest ski resorts in New England, with 578 acres of ski-able trails—Warren is a Vermont destination for all things outdoors. Warren is also home to Mad River Glen, a skier-owned resort that relies almost exclusively on natural snowfall, which is unheard of in the New England snow scene. Mad River Glen is unlike any other ski area in the country due to its alignment with nature and “snow-farming” culture. Mad River Glen is also home to the most popular lift in America, the Single Chair lift. Warren vacation rentals yield a 4.57% cap rate on average.

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Upon arrival in Leavenworth, visitors will immediately notice that nearly every building—including popular grocery stores and restaurants—is fully decked out in Bavarian-style architecture. During the winter, skiers and snowboarders flock to the region’s many mountains, and Leavenworth is blanketed with a layer of snow that makes the town feel even more festive than usual. When travelers aren’t taking in the polka music that drifts through the streets or noshing on German delights like bratwurst, pretzels, and fondue, the nearby mountains await for a day of fun on the mountain, which could include skiing, snowmobiling, or even ice climbing. The market’s 4.36% cap rate is appealing for home buyers, although it might be hard to resist keeping a vacation rental all to yourself in such a picturesque town.

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Shaver Lake has just enough time after the summer months to transform itself into a winter wonderland—and another busy season. From nearly anywhere in the area, snow-capped mountains are the main attraction, and those seeking snow can take to China Peak Mountain Resort overlooking Huntington Lake. While the mountain supports activities of all kinds, it’s a major draw for snowmobilers looking to experience the most beautiful trails in the Sierras. Sprawling lakefront homes offer plenty of space for families and large groups, and lead to a median home sale price of over $600,000.

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Nestled among the pines, Big Bear City vacation homes are ideal for a mountaintop escape from the daily grind. Big Bear lies at the heart of the San Bernardino National Forest less than 100 miles east of Hollywood, with thousands of potential guests to the area just a short drive away. Big Bear’s twin properties, Snow Summit and Bear Mountain, are destinations that offer incredible scenic views and outdoor adventures. Much like Los Angeles, Big Bear offers a ton of events for kids and adults, including Movies in the Meadow, Rail Jams, and night ski sessions. Big Bear is another destination that draws large groups, so buyers should seek homes with multiple bedrooms. However, you can find those homes for a median home sale price of under $300,000.

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