About a decade ago, my wife and I started spending a week in the Hamptons each June with a group of other families at a charmingly run-down collection of converted farm buildings. The place is like a little pocket of the Catskills that got lost in chichi eastern Long Island: It’s pleasingly rustic and disheveled, but the neighbors own professional sports teams and keep Serra sculptures on lawns large enough for their players to scrimmage. It’s one of those word-of-mouth rentals (I’ve been asked not to name it), passed around through the years among like-minded NYC creatives. Days have a pleasing sameness, revolving around the divine local beaches and cooking communal alfresco meals utilizing the compound’s multiple kitchens and barbecues before sitting by the fire with a glass of whatever’s being poured while the june bugs twinkle.
I dug this getaway when I was younger and childless, but as our group of friends has aged and had babies and migrated out of New York City to the suburbs or California, it has come to mean so much more—particularly now that my kids are old enough to look forward to going each summer. The pandemic took it from us last year, so it was especially sweet this summer to see my little ones reunited with friends who’d grown a head since the last time we saw them and showed up with new haircuts, new books, new lingo. And it was sweet for me, too, to have a dear chef friend tutor me on my knife skills as we worked together prepping larb and bun for the Southeast Asian-themed night or to sit up till midnight under the stars talking about late-’70s Dylan and the Brooklyn Nets with a couple of dudes. And it was sweet for all of us to come together and see that we’d all made it through this dark time in the world and know that we could keep coming together like this as our children grow taller and the lines around our eyes grow deeper.
So sweet, in fact, that a bunch of us plan to do it again soon, at a converted boys camp on Lake Pemaquid in MidCoast Maine, where we’ll once again cook and swim and sit by the fire. In my life so far, outside of the those weeks in the Hamptons, I’ve really only taken part in these kinds of big group rentals for destination weddings. But our cohort has pretty much aged out of weddings, and our lives have taken us farther and farther apart from one another, so we need weeks like these to come back together, to eat, to check up on each other. There are email threads going right now about Taos, Andros, Mallorca. Who knows where we’ll meet up next.
More amazing rentals for multifamily retreats
Additional reporting by Meredith Carey.
This article appeared in the September/October 2021 issue of Condé Nast Traveler. Subscribe to the magazine here.
https://www.cntraveler.com/story/multifamily-vacation-rentals-big-enough-for-your-whole-crew-and-then-some