On The Road

Seven Legendary Houses To Rent In The Hamptons

Swap the hotel for the storied halls of these iconic Long Island properties

  • 2040 Meadow Lane. Photograph courtesy of Breitenbach Advisory

Near Georgica Pond in The Hamptons, there’s a shingled 19th-century mansion on two acres with a pool and trellised patio. In the mid-1970s, the house was the setting of Grey Gardens, a documentary about the eccentric Ms Edith Bouvier Beale and her daughter, also named Edith – relatives of Ms Jackie Kennedy Onassis – who’d become hermits and took strange delight in what can only be described as a serious raccoon problem. The house was bought in 1979 and renovated by Washington Post editor Mr Ben Bradlee, of Watergate fame. Following his death in 2014, the legendary newsman’s widow listed the property for $20m.

Grey Gardens embodies much of what makes the Hamptons so very aspirational: bygone indie vibes; gilded names; enormous amounts of money; and a sense that while the Long Island Rail Road provides a bridge, most of what goes on in New York’s hyper-exclusive beach retreat feels out of reach. And yet, for a few years before it sold in 2017, Grey Gardens was available as a summer rental. Deep-pocketed island-goers could wrap their heads in a sweater and perform a jazz number on the patio, just like “Little Edie” did almost half a century ago.

That’s the beauty of the Hamptons: occasionally, the rental market allows us to inhabit privileged spaces rich in backstory and celebrity aura. Sure, the latest million-dollar reno job has scrubbed off some of the history, but it’s also resulted in a bathroom upgrade and a lovely kitchen island, and so one hesitates to complain. In that spirit, and in honour of procrastinators everywhere, we rounded up some of the most magical places that are still – remarkably – available for summer.

01. Mr Richard Avedon’s clifftop compound

  • Photograph courtesy of Douglas Elliman

430 Old Montauk Highway, Montauk

Photographer Mr Richard Avedon had this cedar-shingled beach compound built in 1980, when he was pushing 60 and sitting comfortably atop the worlds of fine art and fashion. Mr Avedon was a high-profile Montauk homeowner back when the furthest-east town in the Hamptons was favoured by elite bohemians such as Messrs Peter Beard and Julian Schnabel, but hadn’t yet been discovered by rosé-guzzling hipster crowds. Twice separated, he preferred sharing the place with his son’s family to staying there alone. Mr Avedon sold the clifftop property in 2000; the current owner, an architect, renovated it a decade ago. Rent it and you’ll get the guest cottage where Mr Avedon stayed, a fire pit, a pool and, best of all, a private beach that’s accessible via staircase. Also included: a legacy of vacation photos that your own snaps will never hold a candle to.

What to pack

  • Loro Piana Stretch-Cotton Jersey Zip-Up Hoodie

  • Derek Rose Bali Wide-Leg Mid-Length Striped Swim Shorts

02. The A-list windmill

  • Photograph courtesy of Douglas Elliman

64 Deep Lane, Amagansett

This is the house for the man who “has everything, but doesn’t have a windmill”. That’s how a broker pitched this one-of-a-kind Amagansett cottage back when it was on the market seven years ago. Now, it’s an absurdly cute summer rental with a history of celebrity tenants: Mr Kurt Vonnegut lived (and presumably wrote) here, and the actor Mr Terence Stamp was in residence for a time in the 1990s. Most glamorously, Mr Arthur Miller and Ms Marilyn Monroe occupied the house briefly in the late 1950s, shortly after the 19th-century windmill’s then-owner, Fabergé Perfumes founder Mr Samuel Rubin, had it converted into a guesthouse. Then, as now, a sense of privacy was central to the Windmill House’s appeal. It sits on 5.5 acres at the end of a long driveway and the only neighbour is the farm for which it was originally built in 1830.

What to pack

  • A.P.C. Slim-Fit Striped Wool Sweater

  • De Bonne Facture Pleated Brushed-Cotton Bermuda Shorts

03. The playwright’s retreat

  • Photograph courtesy of The Corcoran Group

223 Suffolk Street, Sag Harbor

From the outside at least, this 1840s clapboard house epitomises the understated charm of Sag Harbor, which is often said to resemble a New England coastal town (in contrast to its showily hedged-off Hamptons neighbours). Until recently, it belonged to Mr Lanford Wilson, a Pulitzer Prize-winning playwright who split his time between Manhattan and Long Island. Mr Wilson was a local legend, a champion of the city’s Off-Off-Broadway theatre scene and a formidable collector of outsider art. He planted a prolific garden, apparently without the benefit of paid help. In other words, he was old-school Hamptons. Following Mr Wilson’s death, the house’s new owner – former Northern Ireland MP Mr Shaun Woodward – completely redid the interiors in 2012. It’s now a handsome, five-bedroom rental whose amenities include a media room and gym, plus an additional two-bed, two-bath guest cottage.

What to pack

  • Mr P. Twill-Trimmed Striped Cotton-Jersey Rugby Shirt

  • Onia Aiden Slim-Fit Cotton-Twill Drawstring Chino Shorts

04. A Reagan-era classic

  • Photograph courtesy of Breitenbach Advisory

2040 Meadow Lane, Southampton

This 7,500sq ft mansion boasts a pool, tennis court, oceanfront views and nearly four acres of land – just your typical Meadow Lane spread. The neighbours on this prize strip of Southampton dunes include Mr Calvin Klein, hotelier Mr Ian Schrager and some of the country’s wealthiest Wall Street types. Appropriately, perhaps, “Whitecaps” is a product of the 1980s. It was built in 1983 by neo-traditional Hamptons architect Mr Eugene Futterman, essentially as a replica of a 19th-century Southampton cottage that had washed away in a hurricane decades earlier. With its vaguely Gordon Gekko feel, the house is now a different kind of retro.

What to pack

  • Orlebar Brown Bulldog Mid-Length Striped Seersucker Swim Shorts

  • Birkenstock Arizona Oiled-Nubuck Sandals

05. A Miami-style beach house

  • Photograph by RISE Media, courtesy of The Corcoran Group

49 East Beach Drive, Southampton

This sleek white box of a beach house looks straight out of southern Florida. It has, in fact, stood in for a Miami bachelorette-party rental in the 2017 comedy Rough Night. (The film stars Ms Scarlett Johansson, who perhaps found the location convenient from her home in Amagansett.) The house served as the locale for a major plot point, during which a male stripper meets a grisly end. With its 22ft-high ceilings, water views from every room, and monochrome blank-canvas feel, this is one of the most Instagrammable properties on the rental market.

What to pack

  • Loewe + Paula's Ibiza Camp-Collar Floral-Print Cotton-Gauze Shirt

  • Mr Leight Hanalei S D-Frame Acetate Sunglasses

06. A geometric marvel

  • Photograph courtesy of Brown Harris Stevens

615 Dune Road, Westhampton

This Modernist icon has been turning heads since 1958, when architect Mr Andrew Geller applied his considerable talents to an innovative, space-efficient beach shack built on the comparatively humble mid-century Hamptons scale. Its distinctive profile has earned it many an affectionate nickname over the years, among them the “Square Bra”, the “Milk Carton” and the “Reclining Picasso”. The “Double Diamond” house, as it’s also called, narrowly avoided demolition a few years back; the owner, a descendant of the original commissioning family, changed his mind about razing it, and now includes this quirky 600sq ft house for anyone that rents the adjacent and much larger five-bedroom property.

What to pack

  • Frescobol Carioca Arch Wide-Leg Short-Length Printed Swim Shorts

  • Orlebar Brown Seymour Logo-Detailed Cotton-Terry Beach Towel

07. A local legend’s dream home

  • Photograph courtesy of The Corcoran Group

132 Briar Patch Road, East Hampton

Behold, a Japanese-modernist house that’s jacked up on pilings for a view over the treetops and onto the eminently name-droppable Georgica Pond and the ocean beyond – someone here knew what she was doing. That someone was Ms Tina Fredericks, and for three decades she reigned as the East End’s “Realtor to the Stars”. German-born Ms Fredericks, who began her career as an art director, took the likes of Mr Jerry Seinfeld, Mr Tom Wolfe and Mr John Lennon and Ms Yoko Ono house-shopping, sometimes in her Ford Windstar minivan. Her own dream house was completed when she was in her late seventies, and was many years in the making. It’s got an open plan with plenty of decks and skylights, and manages to be six-storeys tall without feeling oversized. The architect has described this five-bedroom, six-bath beauty as “an un-Hampton house”. That statement doesn’t apply to the rental fee, unfortunately.

What to pack

  • Sperry Authentic Original Leather Boat Shoes

Vacation essentials

  • Aesop SPF50 Protective Body Lotion, 150ml

  • Orlebar Brown Haston Rubber and Cork Flip Flops

  • Frescobol Carioca Trancoso Wooden Beach Bat and Ball Set

  • The Row + Oliver Peoples Victory LA Aviator-Style Silver-Tone Titanium Polarised Sunglasses

  • Bang & Olufsen Beoplay E8 2.0 Truly Wireless Ear Buds

  • Frescobol Carioca Striped Linen Towel