Multi-family vacation rentals big enough for your whole crew (and more)

About a decade ago, my wife and I began spending a week in the Hamptons every June with a group of other families in a charming, ramshackle collection of converted farm buildings. The place is like a small pocket of the Catskills lost in the chichi of eastern Long Island: it’s pleasantly rustic and disheveled, but the neighbors own professional sports teams and keep Serra sculptures on lawns. large enough for their players to compete against. This is one of those word-of-mouth rentals (I was asked not to name it), passed down over the years among like-minded New York creatives. The days have a pleasant sameness, revolving around divine local beaches and cooking communal meals al fresco using the resort’s multiple kitchens and barbecues before sitting by the fire with a glass of whatever is poured in while the june insects sparkle.

Lunch at Wandawega

Aimee Mazzenga

The treehouse of the camp, in the middle of the park

Bob Coscarelli

I dug this getaway when I was younger and childless, but as our group of friends got older and had babies and migrated from New York to the suburbs or California, it made a lot more sense. , especially now that my kids are old enough to look forward to going there every summer. The pandemic took it from us last year, so it was especially nice this summer to see my little ones reunited with friends who had grown since we last saw them and showed up with new cuts of hair, new books, new jargon. And it was nice for me too to have a dear chef friend teach me my knife skills as we worked together making the larb and bun for the South Asian themed party. Southeast or sit till midnight under the stars talking about late-’70s Dylan and the Brooklyn Nets with a few dudes. And it was nice for all of us to come together and see that we’ve all been through this dark time in the world and know that we can continue to come together like this as our children grow up and the wrinkles around our eyes fade. deepen.

So nice, in fact, that a group of us are planning to do it again soon, at a converted boys’ camp on Lake Pemaquid in MidCoast Maine, where we’ll once again cook, swim, and sit by the fire. In my life so far, outside of those weeks in the Hamptons, I’ve only really been in those kinds of large group rentals for destination weddings. But our cohort has pretty much aged since the weddings, and our lives have taken us further and further apart, so we need weeks like these to get together, eat, check on each other. There are currently threads on Taos, Andros, Mallorca. Who knows where we’ll end up next.

Wandawega’s A-frame tent cabins have cots and loungers

Kate Berry

Outside the historic Wandawega old dormitory

Jennifer Lawrence

More Amazing Rentals for Multi-Family Retreats

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Courtesy of Airbnb

Camp Wandawega

Elkhorn, Wis.

First opened as a speakeasy two hours north of Chicago, then reopened as a resort in the 1950s, Camp Wandawega offers three-bedroom lakeside cabins, rustic dorms that sleep up to 24 people or the modern two-bedroom Hillhouse. All include access to summer camp must-haves like fishing, canoeing, hiking, archery, and more. Cabins from $650 per night.

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Scarp Ridge Lodge

Ridge Butte, Colorado

Find relaxing mountain elegance behind an old saloon front in this six-bedroom getaway from Eleven Experience. They’ve thought of everything from a seven-bed dorm for the kids to an oxygen-enriched air system to help you adjust to the nearly 9,000-foot altitude. Relax after exploring the summer hiking trails and winter slopes of Crested Butte in the indoor saltwater pool, steam room or rooftop hot tub. $19,900 per night based on 10 people (maximum occupancy is 14).

Airbnbs Church

Courtesy of Airbnb


Pyrgos, Greece

Located on one of the highest points of Pirgos, just minutes from the beach on the Mani peninsula and just over three hours southwest of Athens, this former 19th century monastery converted into a house of Five-bedroom vacation split between two semi-detached buildings offers incredible views. from its private rooftop balcony. There is room for everyone, between the main kitchen, the airy courtyard, the olive garden and the multiple original stone living areas. From $450 per night for up to 13 people.

exterior of Villa La Selva Giardino del Belvedere with tables laid.  branches in the foreground.

Courtesy of La Selva Giardino del Belvedere

La Selva Belvedere Garden

Montgonzi, Italy

This 17th-century luxury estate with three villas, about an hour’s drive from Florence, has something for everyone: a private saltwater pool, 45 acres of olive groves, pizza ovens (yes, plus one!), views of the Tuscan countryside from every angle, and even a stone amphitheater. Be sure to coordinate a chef-prepared dinner (or at the very least a private pasta-making lesson) during your stay. From $980 per night for up to 10 people.

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Courtesy of Airbnb

blue house

Tamarindo, Costa Rica

Whether you’re in the infinity pool, standing on one of the balconies, or inside the bright living room, this five-bedroom cliffside Airbnb offers sweeping views of Tamarindo Bay to the west coast and forest surrounding tropical. But the best outlook comes from the two pagoda-style wooden bungalows – each with its own bedroom, bathroom and outdoor shower – a short walk from the main villa, all on one and a half acres, which feels like an escape full of reality. From $1,100 for up to 10 guests.

Additional reporting by Meredith Carey.

This article originally appeared in the September/October 2021 issue of Condé Nast Traveler. Subscribe to the magazine here.

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