For the recurring series, That’s Debatable, we take on a contentious issue of the day and present two spirited arguments—one in favor and the other emphatically opposed.

BUY: WHAT CAN BE MORE RELIABLY RELAXING THAN RETURNING TO THE SAME HOUSE TIME AND AGAIN?

It’s a freezing winter morning in Vermont’s Green Mountains, and I wake up in a comfortable bed, in an old farmhouse with an exposed post-and-beam frame that’s been wrapped to keep the heat in. The sun bounces off the snow outside; inside, it is toasty and dry (unlike most...

For the recurring series, That’s Debatable, we take on a contentious issue of the day and present two spirited arguments—one in favor and the other emphatically opposed.

BUY: WHAT CAN BE MORE RELIABLY RELAXING THAN RETURNING TO THE SAME HOUSE TIME AND AGAIN?

It’s a freezing winter morning in Vermont’s Green Mountains, and I wake up in a comfortable bed, in an old farmhouse with an exposed post-and-beam frame that’s been wrapped to keep the heat in. The sun bounces off the snow outside; inside, it is toasty and dry (unlike most local vacation rentals; I recall a few musty 1970s chalets). My husband and I bought a fixer-upper on a beautiful property on Stratton Mountain in 2014 and spent a year renovating. We chose to own for the same reason real-estate agent Cheyanne Pugliese, of Stratton’s Wohler Realty Group, says most of her clients do—to have a space for friends or family to gather with maximum relaxation and minimum logistics.

Downstairs, my friends are sleeping in the guest bedroom (when you have a house, you have a lot of friends). Their kids are upstairs with mine in the bunk room (your kids have people to play with on vacation, too). We all decided to come at the last minute to catch a weekend with good snow (good luck finding a rental under those conditions), and I’m about to make breakfast. I brought the milk and eggs with me, but I know the kitchen is stocked with all the other ingredients I’ll need for pancakes. You could say I’m home, but this place is better than my real home—clean, clutter-free and devoted to fun. I’m inspired to keep it that way because of how much I love it.

Illustration: Mike Ellis

It wasn’t always this way. We used to travel, but while I like to be in new places, I don’t like to rent lodgings. Every hotel room has its own problem: the rattling mini fridge, the arctic-wind AC, the impossibly complicated lighting system, the required app, the windows that don’t open or don’t close, the single mosquito. We once stayed with my parents in a design-focused hotel overlooking the Ponte Vecchio in Florence, and my father was upset because the marble-slab statement sink was such that he couldn’t wash his socks. There’s always something.

You think by scoring an apartment rental in a neighborhood, you’ll be living like a local, but in reality, you’re just passing through. By staying put on Stratton, our family learned new things. Our winter home became our summer home, and our summer activities changed us. Both children now swim for a Brooklyn team, a skill they learned in Vermont. I started hiking. My husband picked up split-boarding to make the most of the mountains after the lifts close.

Owning even makes financial sense. Our carrying costs are about what we were spending on vacations for two adults and two children, and the house was an investment. Ms. Pugliese says the younger generation of second-home owners is more inclined to rent their vacation homes to others when the places are not being used, and cover their costs that way. She also sees clients who team up with friends; one buys a beach house, the other a ski house, and they swap, defying the adage that “Once you buy a house you have to go there.” To that old chestnut, though, I say “No problem.” I’ll come here anytime. —Valerie Stivers

RENT: WHY BURDEN YOURSELF WITH A SECOND HOME WHEN THERE ARE SO MANY ATTRACTIVE VACATION RENTALS?

Most folks don’t go cattle shopping in Japan just for a Wagyu steak. You could hypothetically own a supercar, but you can also just drive one for a weekend for a few hundred bucks a day. Vinyl records are also great, but once you get locked into a serious collection, you can quickly find yourself buying high-fidelity turntables and even sexy shelving units to show off all the albums whose songs you could easily stream from your phone for a small fee. It’s not my place to tell you how to spend your discretionary real estate money, but as someone who practices what he preaches, I can offer advice: You could buy a vacation home, but I’d rather rent because vacation homeownership is, to me, the vinyl record collection of finding respite.

Homes, including vacation homes, come with unexpected costs. The average household spending on home services, including improvement, maintenance and emergency costs, rose from an average of $9,081 in 2019 to $13,138 last year, according to a survey from HomeAdvisor, a home-repair referral site. That kind of budget is plenty for a week or so in Hawaii, where the median price of a single family home is moving toward $800,000. And, dare I say, Hawaii could get boring after your 10th time visiting your own property there. At the very least, the investment could keep you from discovering other worthwhile places to dip your toes. Take the beachside house my wife and I rented last summer in Sandestin, Fla., a five-hour drive from our home in Atlanta. With its ocean views, proximity to the shoreline, top-tier kitchen appliances and spa-inspired showers, that wonderful Sandestin house made me feel like I’d freed myself from everything that had grown all-too-familiar because of the pandemic’s lockdown mandates. But how liberated would I have felt if I’d had to worry about replacing a part for those high-end kitchen appliances? Or fixing a leak in that spalike shower?

Illustration: Mike Ellis

Renting a vacation home also means you can trade the beach for the mountains on a whim. For our anniversary, my wife and I drove to the town of Suches, Ga., and stayed in a tiny cabin owned by the vacation-rental company Getaway. With its large windows overlooking the Appalachian foothills, the cabin seemed far more spacious than its small footprint suggested. It was an amazing departure from the norm—one we’re planning to repeat soon because, for two nights, we dropped less than $300, as opposed to paying $12,000 for an acre of Suches mountain dirt, plus the cost of a home.

Perhaps you’re looking for a property that will let you get away for a few weeks every year but potentially turn a profit at some point in the future. Sure, property values for homes with built-in R&R are trending in the right direction. But that’s not a vacation; it’s an investment that will ultimately become a house you’ll be trying to sell for a profit.

I don’t mean to sound like a downer. You deserve your vacation home and its gorgeous sunsets, glistening waters, rolling hills, whatever. But you can borrow that place for less money and less responsibility. After all, if it’s really your home, is it really even a vacation? —Mike Jordan

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