Lavish Poolside Apartment in East Hampton
The Hamptons, USA
East Hampton
Private poolHot tub
From $9,775 per night
Photo by Sarah O'SheaDune-backed beaches and shingled villages at Long Island's end
The Hamptons string along the South Fork of Long Island, a run of shingled villages, farm fields and Atlantic beaches from Southampton out to Montauk. A private estate here is the definitive way to do it: heated pool, lawn and hedges of your own, with the beach, the farm stands and the social calendar minutes away.
Updated September 2026
- Ocean beaches regularly ranked among America's finest, from Coopers Beach to Main Beach
- Village life in Southampton, Bridgehampton, East Hampton and Sag Harbor
- Montauk's lighthouse, surf breaks and fishing-town energy
- Farm stands, vineyards and a celebrated seasonal food scene
- Gated estates and villas with heated pools, lawns and total privacy
Known forAtlantic ocean beaches, shingled estates, Sag Harbor's whaling-port charm, Montauk surf, farm stands and vineyards
Best time to visitMemorial Day to Labor Day for the classic season; September and October for warm sea, harvest and calm
Nearest airportNew York JFK and LaGuardia (LGA), around two to three hours by road; East Hampton Town Airport (HTO) for private aviation
Ideal forFamilies, groups of friends and city escapees seeking beach-and-estate summers
Expansive Pool House in East Hamptons
The Hamptons, USA
East Hampton
Private pool
From $3,162 per night
Stylish Retreat House in The Hamptons
The Hamptons, USA
East Hampton
From $1,552 per night
3homes available
3–8bedrooms
up to 14guests
2with a pool
The Hamptons in pictures
What's on in The Hamptons
- October
Hamptons International Film Festival
A respected festival of premieres, documentaries and talks centred on East Hampton over the Columbus Day weekend. It pairs beautifully with the East End's golden autumn.
- Late August to early September
Hampton Classic Horse Show
One of America's premier show-jumping events, staged in Bridgehampton in the week before Labor Day. Grand-prix Sunday is the social and sporting climax of the Hamptons summer.
- August
Artists & Writers Charity Softball Game
An East Hampton tradition since 1948, when painters, novelists and celebrities face off for charity. A quirky, beloved fixture of the August calendar.
- September
Sag Harbor HarborFest
The old whaling port's waterfront festival, with whaleboat races, chowder tastings and village festivities along the wharf. Small-town Americana at its most charming.
The Hamptons through the seasons
- Spring (March – May)
Quiet villages and flowering lanes
The villages wake slowly, beaches are empty for long walks and gardens bloom behind the hedges. A serene preview before the season begins.
- Summer (June – August)
The classic Hamptons season
Warm ocean swimming, farm stands at full tilt, polo, galas and the Hampton Classic. The villages hum and every day ends with a beach sunset.
- Autumn (September – November)
Warm seas, harvest and film
September's ocean is the year's warmest and the crowds are gone. Pumpkin fields, wine harvest and October's film festival make this the insider's season.
- Winter (December – February)
Fireside weekends by an empty ocean
Hushed villages, bracing beach walks and oysters by the fire. A heated private house turns the off-season into a restorative retreat.
All 3 villas in The Hamptons
Every home in The Hamptons that can be booked with Smiling House, as a plain list.
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
The Area and Where to Stay
Each village carries its own character. Southampton is the grande dame, with estate lanes behind tall privet and Coopers Beach at the end of the road. Bridgehampton and Sagaponack sit among open farm fields, horse paddocks and vineyards, handy for the Hampton Classic showgrounds. East Hampton pairs a picture-perfect Main Street with Main Beach, while Sag Harbor, the old whaling port on the bay side, offers wharfside restaurants and a walkable, salty charm. At the island's tip, Montauk is looser and surfier, with dune motels giving way to clifftop views at the 1796 lighthouse. Villas and estates across the villages share the essentials: heated pools, generous lawns, outdoor kitchens and hedge-lined privacy, with beach parking passes and concierge support smoothing the season's logistics.
Things to Do
The beach is the daily ritual: broad, dune-backed Atlantic sand where mornings mean long walks and afternoons mean umbrellas and paddle games. Beyond it, the calendar fills easily. Browse the galleries and boutiques of East Hampton and Sag Harbor, tour the Parrish Art Museum in Water Mill or the Pollock-Krasner House in Springs, and spend a golden hour at the LongHouse Reserve sculpture gardens. Cyclists take the farm roads of Sagaponack, sailors and paddleboarders work the bays, and surfers head for Montauk's Ditch Plains. Deep-sea fishing charters run from Montauk's docks, among the busiest sport-fishing harbours on the East Coast. Summer evenings revolve around benefit galas, polo and the Hampton Classic; your concierge can arrange beach picnics, boats and tee times.
Food and Local Flavour
The East End is farm country, and eating here follows the fields: roadside stands pile up sweet corn, tomatoes and berries all summer, with pumpkins and apples into autumn. Local bays yield clams, oysters and lobster, Montauk's boats land tuna and striped bass, and the lobster roll is practically the regional flag. Wölffer Estate's vineyards in Sagaponack anchor a small but serious local wine scene, with more cellars across the nearby North Fork. Restaurants run from clam shacks and farm-to-table dining rooms to see-and-be-seen village institutions, and booking ahead in season is essential. A private chef at the villa, cooking that morning's catch and farm-stand produce, is the signature Hamptons indulgence.
When to Visit
The classic season runs Memorial Day to Labor Day, when the villages hum, the ocean warms and the social calendar peaks around August's Hampton Classic. July and August are glorious but busy, with traffic and restaurant bookings to plan around. September may be the connoisseur's month: the sea is at its warmest, the crowds thin, the light turns golden and the harvest arrives at the farm stands, capped by the film festival in October. Late spring offers flowering villages and quiet beaches, while winter is hushed and atmospheric, ideal for fireside weekends in a well-heated house. A private villa makes every season self-sufficient.
Getting There
From Manhattan, the drive along the Long Island Expressway and Route 27 takes around two to three hours depending on season and traffic. The Long Island Rail Road's Montauk Branch and the Hampton Jitney coach serve the villages directly, and seasonal helicopter and seaplane services shorten the trip to under an hour. International travellers fly into New York JFK or LaGuardia (LGA), with East Hampton Town Airport (HTO) handling private aviation a few minutes from the villages. Once here, a car is essential for beach runs, farm stands and village-hopping; your concierge can arrange chauffeured transfers.