This could be the summer you meet your soul mate—the real-estate version, anyway.  The commitment to buy a vacation home, with all the headaches and expenses that come with upkeep and maintenance, can be as daunting as entering into a serious relationship. It had better be right. Home buyers often make the same mistakes as daters: They act on impulse without thinking about the long term; they choose places that seem great on paper but aren’t really right for them; and they don’t take into account how much it will all cost.  So, how to find the right match for you? Here’s a simplified guide to finding your dream summer getaway—with long-term potential.  You are: Fifty-something foodie with sophisticated taste in wine, art and music and a green thumb. Kids are grown or are at camp.  Your match: Napa Valley estate with vegetable garden.  Median listing price for luxury market: $5.27 million  Change in price from 2015: +42.9%*  If your ideal summer afternoon involves sipping wine over a garden-to-table meal, listening to pleasant music and gazing at vineyards, then Napa is the spot. Sophisticated wine, food, art and design, and music abound. There are lots of golf courses, too. But fancy food and wine events don’t mix well with young children or teenagers.  “It’s adult heaven. For children it can be boring,” says Julie Husic, whose second home in Napa is on 120 acres and includes a main house, pool house, guesthouse and three vineyards. When her two sons were young she parked them at the swimming pool at two different clubs. The median age in Napa is 39—five years more than the median for California as a whole.  Adult paradise comes at a price: After bottoming out in 2010, Napa County’s housing market has been on a steady rise, currently ranked as the ninth least affordable in the U.S., according to RealtyTrac’s first-quarter 2016 Home Affordability Index. A spec house is on the market in St. Helena for $38 million.  It’s easy to get drawn into the local enthusiasm about farm-to-table cuisine, whether that means making your own wine, olive oil or just dinner from your garden. Mrs. Husic and her husband bought their estate in 1995 expecting to use it to relax; now they produce six wines from their vineyards.  Another resident, Diane Morris, says the vegetable garden at the estate she bought in Napa almost 30 years ago was small; now she has 200 olive trees, hundreds of vegetable plants, and pear and citrus trees.  “It’s a very fertile place,” she says. Her St. Helena home—a 7.2-acre historic vineyard estate with a six-bedroom main home, guesthouse, a pool house, a caretaker’s house and carriage-style garage—is listed for $15 million.  You are: Thirty-something parents with children who need room to roam. Nostalgic for the summers of your youth. Loves being outdoors, but must find a good restaurant at the end of the day.  Your match: Lavish but rustic cabin in Falmouth, Maine.  Median listing price for luxury market: $975,000  Change in price from 2015: -2.5%  Falmouth isn’t at the top of the list of well-known Maine summer spots. That would be Kennebunkport or Mount Desert Island. But Kim Nemser, 36, and her husband, Adam, 36, who live in an apartment in New York City, were looking for a place where their children, 4 and 6, could run around. Falmouth emerged as the top choice.  “We wanted something really different—not a summer place but a community,” says Ms. Nemser, who bought a house in 2014 that they are renovating.  The dichotomies in Falmouth attract buyers. It’s on the Maine coast with access to rugged islands, yet it is also 7 miles from the airport in Portland, where there are direct flights from New York.  It’s easy to go into Portland for upscale restaurants and shops and entertainment, but there is a small-town feel in Falmouth itself: old-style New England with traditional architecture, a classic country club, blueberry picking, nature walks and sailing opportunities.  The overall median sale price for Falmouth homes in 2015 was $484,000, up less than 10% from a year earlier and about the same level it was a decade ago, in 2006.  Al and Dawn Hoffman bought their 10-bedroom, seven-bathroom, 9,000-square-foot house on Clapboard Island West in 1999 for $1.65 million. It is accessible only by boat. Ms. Hoffman, 60, and Mr. Hoffman, 82, renovated the house by keeping it faithful to its history while adding modern energy systems and other upgrades. They have used the house every summer for entertaining. He is a real-estate developer and former U.S. ambassador to Portugal. In 2005, they bought a house in mainland Falmouth. Two years ago they listed their island house for $6.5 million; it’s now on the market for $5.5 million.  You Are: Affluent traditionalist with a love of all things New England.  Your Match: Shingle-style home in Nantucket.  Median listing price for luxury market: $7.6 million  Change in price from 2015: +37.3%  Nantucket has always had an understated see-and-be-seen philanthropic party scene, where high-level politicians and tech executives are spotted at lawn parties and fancy restaurants in the summer.  Still, it isn’t hard to avoid the social scene for those who just want to relax by the waves. “I can get on a bike, find a dirt road and get to an empty beach,” says Judy Lindeman Brasher, senior development officer at the Winsor School in Boston. Half the island’s land is held in permanent conservation.  Longtime summer-home owners often fret about the transition from a stately island with simple homes to one packed with huge mansions. The summer population is now more than 50,000. That means lots of traffic.  Sara Cornell loves the island so much she recently started spending the whole summer there at her partner’s house. But there are some drawbacks: “I have to go grocery shopping at 5 a.m.,” she says, referring to the difficulty getting a parking spot at any other time at the island’s Stop & Shop. Maintenance is also an issue, adds Ms. Cornell, a blogger who lives in Chestnut Hill, Mass. Basic landscaping and plumbing services can be expensive. The couple hires a year-round caretaker to see to the house in the off-season.  Richard Savery, 61, built his own custom-designed, nine bedroom house in 2007. He’s now selling it for $7 million because he is getting close to retirement.  Nantucket has a severe shortage of affordable housing. The median sales price for all homes on Nantucket last year was $1.7 million, while median family income was $92,800. One solution the town is considering is a real-estate excise tax.  You are: A tech-savvy male with libertarian leanings. Loves hiking, fishing and mountain-climbing.  Your Match: Mountain hideaway in Jackson, Wyo.  Median listing price for luxury market: $4.87 million  Change in price from 2015: -1.2%  Forget the stunning vistas, world-class fly fishing and unparalleled access to national parks. Jackson’s most attractive feature for many home buyers? Its tax profile.  “It’s a huge incentive,” says Audrey William, of Jackson Hole Sotheby’s International Realty.  Wyoming has no state income taxes, no inheritance or estate taxes, no state gift tax, relatively low property taxes, no excise taxes and no tax on the sale of real estate, says Chris Reimer, a tax attorney in Jackson Hole.  Prices in the resort area of Jackson Hole (which includes Jackson and surrounding areas) have remained robust, even as other Western resort communities have seen a slowdown.  In 2015, the average sale price for all homes in Jackson Hole rose 31.2% compared with the previous year. In the same period, prices fell 10.2% in Montana’s Big Sky, 2.2% in Colorado’s Vail Valley and 5% in Lake Tahoe, Calif., according to a report from Sotheby’s International Realty.  Drew Taylor, 64, a former energy-finance and information-technology officer who now does consulting work from home, says he loves that Jackson offers both an immersive nature experience and a vibrant high-tech community.  “You can sit in the middle of the woods and still be on the Internet,” he says.  He bought his 4,700-square-foot home on 5.2 acres in 1996 for $1.1 million. He then spent $1.7 million renovating and updating it, putting in fiber-optic lighting, electrostatic speakers controlled with a Crestron system, a media room with dupioni silk wallpaper to cancel any echoes or hollow sounds and a Siedle security system. He has it listed for $3.2 million.  (*Note: Available matches and price statistics reflect the top 10% of the market by price, based on active listings for sale on Realtor.com in April 2016.)
Looking for your perfect match in a vacation home? Mansion’s guide to real-estate romance, whether you’re in the market for a beachy retreat or mountain getaway.