Best places to buy a winter vacation home 2020–2021

With a cap rate of 9.2%, Big Sky can yield big returns for homeowners with an annual gross rental revenue of nearly $80,000. The vacation destination known for endless miles of snowy terrain also ranked first on our 2020 Top 25 Best Places to Buy a Vacation Home report released this summer, and it’s easy to see why. According to the area’s website, they refer to Big Sky country as an “R” destination, meaning it offers guests the opportunity to recreate, reconnect, relax, and rejuvenate—in other words, our ideal vacation scenario. So whether you want to embark on one of the endless adventures that Big Sky has to offer, or are there for the country’s first National Park, you’ll find it all in Southwest Montana.

Number two on our Best Places to Buy a Winter Vacation Home report are the cozy towns that lie within the Poconos region. Like Big Sky, the Poconos are also ripe for outdoor exploration, and the area is considered a four-season destination. And, while the gorgeous waterfalls, stunning lakes, and changing leaves in the fall already provide a romantic backdrop for couples, the Poconos are also home to heart-shaped bathtubs. Yep, you heard that right—the Poconos once held the title of Honeymoon Capital of the World, with heart-shaped tubs popping up in resorts and vacation rentals throughout the area. Whether that’s your design style or a hard pass, the Poconos has plenty of vacation homes and a cap rate of 8.2%.

Often referred to as the Birthplace of American Skiing, Conway oozes New England charm. Depending on how you travel to Conway, getting back in the car might not seem too appealing, but taking a trip through the area is one of the most popular activities—especially when the leaves are showing off their new fall colors. But, if you’ve ever had the urge to climb a mountain—by train, that is—then jump aboard the Mountain Cog Railway and take its one-of-a-kind locomotive up the side of Mount Washington to its tallest peak. While you may not feel like you deserve a treat after letting the train do the work as you take in the views, a stop at the local Soaking Pot is a must. Enjoy a 30- or 60-minute treatment before heading home to your vacation rental, which you could snag for around $230,000.

Skiing. Snowboarding. Snowshoeing. Golfing? While Killington is best known for its miles and miles of diverse winter terrain, it’s a surprise delight come the spring months—when the snow is gone and two PGA golf courses are revealed, along with trails upon trails of hiking and biking routes. Killington, which (according to its residents) also boasts a killer après ski and nightlife, also sports a healthy cap rate of 6.2% and a median home sale price of $218,000, making it a more affordable option for those looking to invest. Best of all, many of the homes we manage offer breathtaking views and outdoor spaces where you can take in the beauty of Vermont.

There are many things we love and appreciate about Vail, but perhaps none are as unique as the way more than 5,000 permanent residents blend harmoniously with another 5,000 or so folks who own vacation homes in one of the most beautiful ski destinations in the world. And what’s even better? Vail somehow still evokes a small-town, cozy feel amid its over-the-top shopping destinations and luxury accommodations. While it is one of the more expensive (okay, fine, the most expensive) of our best places to buy—at an average median home price of nearly $650,000—homes in the area see a cap rate that goes right along with it at 6.1%. And while your vacation rental revenue might be tempting, spending weekends of your own at Blue Sky Basin will be equally so.

Sunny skies beckon most visitors to California with images of surfers and sandy beaches, but for a different dose of the state’s majestic beauty, look toward the mountain town of Big Bear. Self-proclaimed as the best skiing in SoCal, Big Bear has a more laid-back feel than some of the other markets that made our list of the Best Places to Buy a Winter Vacation Home. Perhaps part of the reason for that sense of relaxation is the multiple ways to travel there and avoid the typical traffic jams that plague most of the state. Skiers and snowboarders can get back to their vacation homes more quickly given the alternative routes, just in time to soak in the hot tub with a beverage of their choice. In our case, that’s a Whispering Pines IPA from Big Bear Lake Brewing Co.

An old mining town with a heart of gold, Breckenridge will make you feel right at home at any time of year. Winter is ever-popular, whether you're bundling up to experience Main Street, practicing your mushing skills for dog sledding, or just plain old hitting the slopes. “Breck,” as it’s so fondly called by residents and visitors alike, lands at number seven on our list. For those seeking winter sports outside the norm, look no further than Breckenridge, which offers every type of snow activity possible. Not convinced? Let us know after your snowcat tour. Even so, Breckenridge has no problem attracting visitors year-round, and a vacation home can earn nearly $60,000 in annual gross rental revenue when you decide to share it with guests—just be sure to make it there yourself for good measure.

Champagne powder snow? If that doesn’t perk your ears right up to this mountain town with a ranching culture, we’re just not sure what will. This particular brand of snow, whose nickname was coined by rancher Joe McElroy when the snow “tickled his nose like champagne,” is only found in Steamboat Springs. Of course, it’s not actually champagne (bummer), but it does have a lower water content that sits around 6%. Travel outside the area and you’re looking at 15% by comparison. Another big draw is the number of nonstop flights to the area, including a shuttle from Denver. Guests to your vacation home will have no excuse when they’re dying to get out of the city.

Looking for a basecamp for attractions like the Winter Park Ski Resort, Rocky Mountain National Park, Grand Lake, and the Hot Sulphur Springs? They’re all within a 20-mile radius of Granby (that’s right, no “d”), Colorado. Granby is a four-season destination through and through, but it shines in the summer and winter with its far-reaching list of outdoor activities. Once considered a sleepy mountain town, Granby has made “it” lists in recent years as a desirable destination for families and friends, since it’s nestled between two other popular Colorado destinations: Winter Park and Grand Lake. Vacation homes in Granby vary from condos and cabins both well loved and brand new, to ski-style lodges built for 10+ guests.

Mammoth Lakes, California, is such a special place, they’ve created their own season: “swinter.” As you can probably imagine, this newly minted season (March through June) combines summer and winter, and it’s wildly popular among guests to the area. So while winter is reserved for the appropriate snowfall activities, swinter is a magical time where you can be up on the mountain in the morning and kayaking on the lake in the afternoon—an ideal scenario for any adventure seeker looking to pack multiple activities into one day. You can snag your very own Mammoth Lakes getaway for just under $500,000, and it’ll give you back a healthy 4.8% cap rate.