Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
300+ point inspection
Every Luxury Retreats home is personally verified to be in pristine condition.
On-trip care, 24/7
Premium, on-demand assistance for any question, at any time of day.
Flexible bookings in The Hamptons
Cancel penalty free until 14 days before arrival for trips with checkout through Sep 15 2020
19 – 33 of 33 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.
Planning a vacation in the Hamptons? We’re here to help!
Manhattan in the summer – 85 degrees and more than a million and a half other hot, sweaty bods cramping your style? It’s no wonder NYC’s well-heeled residents hightail it to the Hamptons every chance they get from May all the way through to October, retreating to homes that stand out as some of the most expensive real estate in the country. The postcard-pretty villages along the east end of Long Island’s South Fork, with their shingle houses and New England feel, are strung along roads dotted with farm stands and no-frills seafood joints – a reminder of the farming and fishing history of this now high-end hideaway. Wide-open Atlantic beaches, rolling vineyards, and a thriving artistic community are other draws in this perfectly civilized playground.
The sense of space and magnificent, windswept landscapes of the Hamptons have long been a magnet for artists, who have flocked to the east end to escape cramped New York lofts and to take inspiration from the wild and beautiful scenery. In the late 19th century, American Impressionists set up studios here, and in the mid-20th, now-legendary names of the New York School headed this way, among them Roy Lichtenstein and Willem and Elaine de Kooning.
Perhaps the most famous of the bunch is Jackson Pollock, he of the giant, paint-splattered canvases, and if you head out to East Hampton you can visit the house where he created his abstract expressionist masterpieces. In 1945, Pollock married fellow artist Lee Krasner and moved to the Hamptons from New York City. Their home is now the Pollock-Krasner House and Study Center, and the barn where Pollock splashed about still bears witness to his creativity – the studio floor is covered with evidence of the messy forging of Autumn Rhythm, Convergence, Blue Poles and many of his other works painted between 1946 and 1952.
Further west in Water Mill, the Parrish Art Museum is a repository for more than 2,600 works, ranging from early 19th-century landscape paintings through American Impressionism and into the 20th and 21st centuries. Founded in 1898 by a New York lawyer, Samuel Longstreth Parrish, to house his collection of Italian Renaissance paintings and sculptures, the museum was originally housed in a late 19th-century building in Southampton, but in 2012 it reopened in its current Herzog & de Meuron-designed home just a few miles down the road. The massive, barn-like structure provides 12,200 square feet of exhibition space in which to display the museum’s collection of mostly American art, and there’s a cafe and open studio sessions where kids can create artworks inspired by the pieces on display.
Speaking of kids, there’s plenty for families to do out east too. Hank's Farmstand in Southampton and Pumpkintown in Water Mill combine a good ol’ down-home farmstead and a corn-and-pumpkin-themed play park to cover the summer and fall seasons. At the farm stand, there’s sweetcorn, berry and apple picking, as well as local produce to buy. Come fall, Pumpkintown is a riot of orange with a huge range of activities. There’s a towering corn maze to get lost in, wagon and tractor-train rides, calf roping, cow milking, duck and pig races and more, plus hot, buttery roasted corn and addictively good cider donuts.
For something both fun and educational, take the rugrats along to The South Fork Natural History Museum & Nature Center. Here there’s a marine touch tank where kids can learn about the inhabitants of the local waters, holding sea stars, crabs, urchins, and whelks. Outside are the colorful Native Butterfly and Wildflower Gardens, and visitors can take nature walks through the 40-acre Vineyard Field Preserve bordering the museum, and explore the six-mile trail system of the Long Pond Greenbelt, skirting interconnected ponds and wandering through woods and wetlands stuffed with rare plants and animals.
Fruit of the vine
In the Hamptons, rosé rules, and a Long Island wine industry is growing to slake the thirst of all those summer sippers. Croteaux Vineyard, up in the historic North Fork town of Southold, dedicates its entire output to the pink stuff and is the only vineyard in the United States to do so. Stop by its tasting barn, which opens onto a pretty courtyard and serves the vineyard’s Provence-inspired wines – but hurry, one the year’s stock is sold, the winery closes until the start of the new season the following year.
The Wolffer Estate & Vineyard in Sagaponack is another top viticulture destination. The estate – once a potato farm – serves award-winning wines, and sunset on a Friday evening at the alfresco wine stand, overlooking the vines while enjoying live music and sipping Summer in a Bottle Rosé, Noblesse Oblige sparkling or Wolffer Cuvee Cider is a great way to kick off the weekend.
Experience the luxury of our Hamptons rentals
Whether you’re heading to the Hamptons in the height of summer to hit the beach and feast on fish surfside (Coopers Beach and East Hampton Main Beach are both doozies), or coming in the fall to gorge on all that glorious harvest produce, there’s a Hamptons town, village or hamlet that’s just right.
For a taste of old money Hamptons, our houses to rent in Southampton are just the ticket. Sample the delights of the season then head home to your sprawling manor house by the ocean with its swimming pool, hot tub, and balcony perfect for a sit-n-sizzle barbecue as the sun sinks below the horizon.
Homes in Sag Harbor
The old whaling port of Sag Harbor has come a long way from its salty seafaring days, and our Sag Harbor rentals offer modern luxury for a leisurely vacation. Chill out among the shingled windmills and dramatic sand dunes, seek treasure in the lovely old antique shops or just make the most of a gorgeous rental with a gather-round fire pit in its languid grounds and light-filled, beautifully furnished rooms.
Homes in Water Mill
One of the smaller villages, Water Mill is a sleepy hamlet on the route between Southampton and East Hampton. Our Water Mill rentals allow you to make the most of the serene seclusion, playing tennis on your private court perhaps, lounging by the pool sipping a chilled glass of rosé or sitting with your daydreams in the steam room.