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The Best Places to Buy a Vacation Home Across the US

Pro tip: consider rental value as much as a destination you’d enjoy in all four seasons.


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When looking to acquire a vacation home in the U.S., there are three important factors to keep in mind as you start choosing a location: usage, financial value, and contrast to your current home. The first point is simple: are you going to use your vacation home enough? When considering this, you need to take into account proximity to your own home (can you drive up to the vacation home on weekends, or are you willing to frequently take that direct flight?), as well as your genuine fervor for the destination. In terms of financial value, you’ll need to consider the rental market if earning passive income off your property appeals to you, and potential resale value if you’re not keen on keeping the house long term. And finally, you want to focus on creating a contrast between your current home and your aspirational vacation retreat. If you live on the coast, maybe taking to the mountains sounds particularly appealing. If you live in a Manhattan high rise, a sprawling property on Martha’s Vineyard could be the perfect place.

Related: How COVID-19 Has Changed What Buyers Are Looking for in Their Next Luxury Home

As you narrow your search, we’ve collected some of the very best places to buy a vacation home in the country:

Martha’s Vineyard, Massachusetts

Martha’s Vineyard has some of the most coveted real estate opportunities in the northeast. An exclusive market, it’s tricky to break in, but the reward of reveling in waterfront views and feasting on lobster rolls is well worth it. A Martha’s Vineyard home is less about the rental potential, because you’ll want to use the house during high season. It’s value is in the pure luxury and glorious summertime memories that come with owning a home on Martha’s Vineyard.

Lake Tahoe, California

There’s no way to sugar coat this: California state taxes are high and California home prices are higher. And when searching for California vacation homes, you have to pick a lane right off the bat; do you want a coastal, desert, city, wine country, forest, or ski vacation house? Ultimately, to make a vacation home financially worthwhile, you have to steer clear of Los Angeles, Orange County, San Francisco, and Napa Valley. The abundance of places to stay and five-star hotels decreases the vacation rental value, while home prices continue to skyrocket. We’re partial to the opportunity Lake Tahoe presents; it’s a perfect venue for an annual family ski vacation and a beautiful place to host holidays with the whole brood. It’s also a foliage hotspot in the fall and a summer lake town in the warmer weather, and a destination for Oregon, California, and Nevada roadtrippers—all of which up its rental value.

Jackson Hole, Wyoming

Jackson Hole is one of the unique western mountain cities that can actually position itself as a four-season destination. The beauty of sitting right at the door of the Grand Tetons is that travelers really will come year-round, which ups the rental value on Jackson Hole property considerably. A well-situated home in Jackson Hole gets you prime access to skiing Jackson Hole Mountain Resort, while also offering the perfect base camp for exploration in Yellowstone or Grand Tetons National Parks. In addition to outdoor adventure in every season, Jackson Hole is known for its luxurious home on phenomenal parcels of acreage.

Wrightsville Beach, North Carolina

The southern North Carolina coast is not only a stunning stretch of Atlantic shoreline, it’s also a perfect alternative to Myrtle Beach and the more populous South Carolina beach towns. Wrightsville has great local businesses of its own and has the added benefit of being only 15 minutes from Wilmington. For those buying a vacation home for multi-generational family gatherings, North Carolina is well-positioned for those coming from various parts of the north and southeast—it’s driving distance from Washington D.C., Atlanta, and Baltimore, and a short flight from Philadelphia, Boston, New York, and Chicago.

Key Biscayne, Florida

Florida is brimming with vacation home possibilities, from Key West to Boca. We’re advocates of Key Biscayne as a vacation house venue because it offers all the charms of Florida—the sun, the sand, the surf—and all the flair of Miami. And the fact that it’s near a major international airport doesn’t hurt, either. The barrier island has relatively high home prices as compared to the state’s averages, which means to really make a Key Biscayne vacation home a worthwhile investment, you need to spend a substantial part of your year here. Snowbirds looking to flee the northeastern cold in favor of Floridian warmth are often drawn to the area around Miami because it keeps them close to the amenities and dining in South Beach and the culture of Miami—that’s why posting up in Key Biscayne makes sense for the long-term vacation home purchase.

Killington, Vermont

In central Vermont, Killington is, of course, best known for the mountain that brings skiers, snowboarders, and winter sport enthusiasts in droves. Not only is Killington a perfect vacation home for avid skiers, the house price to rental price comparison may work out in the buyer’s favor. According to Business Insider, the median house price is just over $200,000, but the nightly rental rate is $432. Because the rental opportunity is skewed toward the winter, Killington buyers should be equally excited about Vermont summer (which shouldn’t be a tough sell, considering it’s pure magic) before they invest.

Scottsdale, Arizona

Scottsdale offers both desert life and small city life, perfect for the family looking for a vacation home with a pool in walking distance of great coffee shops and local boutiques. Not only does Scottsdale have a buzzing dining scene and lively downtown, the area is also known for exceptional hiking trails, from the McDowell Sonoran Preserve to Pinnacle Peak. A Scottsdale vacation home also has great opportunity for doubling as a rental property—the median sale price is around $500,000, but the average nightly rental rate is $360, and could grow as Scottsdale heats up on the luxury travel scene.


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