Luxury villas in New YorkPhoto by Lilen Diaz

USA and Canada

Luxury Villas in New York

23 properties

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From Hamptons dunes to brownstone streets, New York at leisure

New York State pairs the world's most famous city with one of America's most storied summer coastlines: the Hamptons, at the eastern end of Long Island. Renting a luxury villa here means a hedged estate with a pool in Bridgehampton, a surf-side retreat in Montauk or a design-led townhouse in Brooklyn, each with the space and privacy hotels cannot match.

Updated October 2026

  • Bridgehampton and the Hamptons villages, hedged lanes, farm stands and ocean beaches
  • Montauk, the laid-back surf town at Long Island's wild eastern tip
  • World-class dining, galleries and theatre in Manhattan and Brooklyn
  • Long Island's North Fork wine country, an easy drive from the Hamptons
  • Private-pool estates and townhouses with concierge service, booked direct
Known forThe Hamptons' beaches and estates, Montauk's surf and lighthouse, New York City culture, Long Island wine country
Best time to visitJune to early September for the Hamptons season; September and October for warm seas, harvests and fewer crowds
Nearest airportJFK and Newark (EWR) for international arrivals; Long Island MacArthur (ISP) closer to the Hamptons
Ideal forFamilies and groups summering by the ocean, city-and-beach combiners, food and culture lovers

Villas in New York

GreigEast HamptonGlenfield
23homes available
1–8bedrooms
up to 17guests
2with a pool

Where to stay in New York

Upstate New York6

What's on in New York

  1. October

    Hamptons International Film Festival

    East Hampton's respected film festival brings premieres, directors and awards-season buzz to the villages each autumn, just as the coast turns quiet and golden.

  2. Early November

    New York City Marathon

    The world's largest marathon sweeps through all five boroughs on the first Sunday of November. Watching from Brooklyn's brownstone streets or Central Park's finish is a memorable city day.

  3. Late August to early September

    Hampton Classic Horse Show

    One of America's premier show-jumping events, held on the showgrounds at Bridgehampton in the week before Labor Day. Grandstand Sunday, when the Grand Prix is decided, is the Hamptons' great end-of-summer occasion.

  4. Late August to early September

    US Open Tennis Championships

    The year's final Grand Slam, played at Flushing Meadows in Queens. Evening sessions under the lights are electric, and the tournament pairs naturally with a late-summer Hamptons stay.

New York through the seasons

  1. Spring (March – May)

    The coast reawakens

    Villages reopen, gardens bloom and beaches are empty and windswept. City weeks pair well with quiet early-season Hamptons weekends.

  2. Summer (June – August)

    Classic Hamptons beach season

    Warm Atlantic swimming, farm stands at their peak and the social calendar in full swing from Bridgehampton to Montauk. Book villas well ahead.

  3. Autumn (September – November)

    Golden light and harvest

    Warm seas linger into October, the North Fork harvest arrives and the film festival brings a cultural close to the season. The connoisseur's window.

  4. Winter (December – February)

    City lights and holiday windows

    Manhattan and Brooklyn shine with theatre, museums and holiday displays, while the wintry Hamptons offer log fires and long empty beaches.

All 23 villas in New York

Every home in New York 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

Most of our New York collection lies in the Hamptons, the string of villages along the South Fork of Long Island about two to three hours east of Manhattan. Bridgehampton sits at its heart, all hedged lanes, horse farms and broad Atlantic beaches, with Sag Harbor's old whaling port and East Hampton's elegant main street close by. Further east, Montauk trades manicured lawns for dunes, surf breaks and a working harbour, a wilder, younger take on the coast. Villas here range from shingled estates with pools and tennis courts to modern architectural houses in the dunes. In the city, Brooklyn's brownstone neighbourhoods offer townhouse stays with gardens and quick access to Manhattan. Combining a few city nights with a Hamptons week is the classic New York villa itinerary.

Things to Do

Hamptons days follow a pleasing rhythm: morning farm stands, ocean swims from wide sandy beaches, afternoons by the pool and evenings out in the villages. Surf or paddleboard at Montauk, cycle the flat lanes around Bridgehampton, visit the Parrish Art Museum in Water Mill or take the ferry across to Shelter Island. The North Fork's vineyards make an easy tasting day, and deep-sea fishing charters run from Montauk's harbour. In the city, the Metropolitan Museum, Broadway, Central Park and Brooklyn's food and gallery scenes need no introduction. Your concierge can arrange beach permits, boat charters, tennis coaching, restaurant reservations and drivers, so the logistics of a busy Hamptons summer never touch you.

Food and Local Flavour

Eastern Long Island is genuine farm-and-fish country. Summer brings sweet corn, tomatoes and berries to roadside stands, while Montauk's day boats land tuna, fluke and striped bass, and local waters produce celebrated oysters and clams. Hamptons villages hold everything from clam shacks and lobster rolls to polished dining rooms that migrate out from Manhattan each summer, and the North Fork's wineries pour crisp whites and rosé a short drive away. In the city, New York's restaurant scene is arguably the world's deepest. A private chef at your villa is the easiest way to turn farm-stand produce and just-landed seafood into long summer dinners by the pool.

When to Visit

The Hamptons season runs from Memorial Day at the end of May to Labor Day in early September, when the villages are at their liveliest and every beach day counts. July and August are peak weeks, so villas book far in advance. September and early October are a local secret: the ocean is still warm, the light turns golden, harvest arrives on the North Fork and the crowds thin dramatically. Autumn is also New York City at its best, crisp and cultural. Winter suits city stays, with holiday windows and theatre, while spring sees the coast reawaken. For a classic villa summer, aim for June through September.

Getting There

International travellers arrive via JFK or Newark (EWR), both roughly two to three hours' drive from the Hamptons depending on traffic, with Long Island MacArthur (ISP) a closer domestic option. The Long Island Rail Road and premium coach services run out to the Hamptons villages in season, and helicopter transfers from Manhattan reach East Hampton in under an hour. A car is essential once you are out east, as beaches, farm stands and villages are spread along Route 27. The concierge can arrange chauffeured transfers, helicopter seats and car hire to make the journey effortless.

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