Best places to buy a winter vacation home 2021–2022

The number one ski market on our Best Places to Buy a Winter Vacation Home hits the half pipe in Newry. Though the northeastern part of the country may not come to mind as the best place to hit the slopes, the powder at the Sunday River Resort helps boost the town’s 12.3% cap rate. And, not to be ignored is the Jordan (nope, not that one)—the fastest eight person chair lift in North America—to take you to the top.

Gatlinburg can’t seem to stay off of our Best Places to Buy a Vacation Home lists and has come in at the top for the past few years. Perhaps one winter activity driving guests to the area? The Ober Gatlinburg Mountaintop Park and Aerial Tramway, which not only offers skiing and snowboarding, but ice skating, tubing, and even a ski mountain coaster. But let’s not just focus on the chillier months, Gatlinburg is a year-round destination for travelers and boasts a strong cap rate above 8%.

Down(hill) just one spot from our 2020 Best Places to Buy a Winter Vacation Home report are the ski towns that lie within the Poconos region. And, according to the Poconos Mountains website, which lays claim to modest mountains, deep snow, fast lifts and impeccably groomed trails, it’s no wonder Poconos ranks on our list for the second year in a row. The median home sales price is still under $300,000, making it an attractive buy for first timers in the market.

In the winter months, skiers and snowboarders flock to Wisp Resort in the Western Maryland mountains, where they can glide down 33 slopes totaling 11 miles of terrain. For those who prefer to have their feet firmly on the ground, there are plenty of other winter activities—including hiking to Swallow Falls State Park, partaking in a guided snowshoe tour, and even slushing through the snow on a festive sleigh ride. A median sales price of approximately $440,000 means these dreamy scenarios can be a reality.

Often referred to as the Birthplace of American Skiing, Conway oozes New England charm, drawing a wide variety of visitors to its snowy peaks. In short, it’s a skier and snowboarder delight with more than a dozen ski resorts and Nordic centers within just half an hour of town. Snowshoeing and tubing also abound, but one activity Conway can offer that others cannot? The opportunity to partake in some of the best ice climbing around. A 4.8% cap rate can keep you flush with cash for park fees.

The Montana vacation destination known for endless miles of snowy terrain AND summer time fun is another market that consistently ranks on our Best Places to Buy a Vacation Home lists year after year. Some refer to Big Sky country as an “R” destination, meaning it offers guests the opportunity to recreate, reconnect, relax, and rejuvenate—but it should also count as an “S” destination, for skiing, snowboarding and basically any other activity that involves fluffy white powder. The median home cost in Big Sky has soared since the pandemic, so $850,000 is likely a stretch for most, but we’re still optimistic about the $60,000+ in annual gross vacation rental revenue.

Known largely for the best skiing in SoCal, Big Bear has a more laid-back vibe than some of the other markets that made this year’s Best Places to Buy a Winter Vacation Home report. Skiers and snowboarders will fly through the trails freshly groomed for every type of skier—from little ones testing the magic carpet to advanced participants taking on the Black Diamonds. Buyers are feeling good about Big Bear because of its 4.5% cap rate and annual gross rental revenue of just nearly $39,000.

When a destination describes itself as “life inside a snow globe” there is no doubt that it belongs on our Best Places to Buy a Winter Vacation Home report. For locals, an experience like no other can be found at Echo Ridge, a Nordic ski resort in Lake Chelan Valley, which offers snowmobiling, cross country skiing, snowshoeing and tubing, in addition to the regular downhill fare. With homes available—and lakefront a major plus—around $416,000, Chelan is an ap “peel”ing option in the apple state.

The Okemo Mountain Resort in Ludlow is a true winter wonderland with world-class amenities and terrain options for all levels of skiers and snowboarders. It’s another mountain resort that truly has it all and is accessible for all ages in the Green Mountain State, which is bordered by several highly populated northeastern states. Ludlow is an area where the cap rate may have dipped, but the average daily rate for vacation rentals has increased significantly.

Located in the Blue Ridge Mountains of North Carolina’s High Country, Banner Elk is nicely situated between two major ski resorts—Sugar Mountain and Beech Mountain Resort—and keeps skiers and snowboarders on their toes with a wide variety of terrain. One has North Carolina’s only double Black Diamond run, and the other offers the state’s only mountaintop skybar. Fun for kids can be found just 30 miles away at the East Coast’s largest tubing park, featuring more than 30 lanes.