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Vacation rentals in The Hamptons

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Top-rated vacation rentals in The Hamptons

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home in Southampton
PICTURE PERFECT SOUTHAMPTON HOME-
Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!
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Home in Sagaponack
Amazing Home close to Everything -
Beautiful, designer home with new appliances, seasonal heated pool located just a few short minutes to ocean beaches, Wolffer Vineyard, Bridgehampton/Sag Harbor villages. The home has mature landscaping and pristine. Every attention to detail has been met. Please read the disclosures, guidelines, and rules. No events, no parties, no smoking (We are a smoke free home & property. ) – no exceptions please! Please take a look at the whole listing to be sure this is the right home for you.
Individual Host
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Home in Sag Harbor
Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!
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Vacation rentals for every style

Get the amount of space that is right for you

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Stay near The Hamptons's top sights

Photo of The Clubhouse
The Clubhouse45 locals recommend
Photo of Cedar Point County Park
Cedar Point County Park48 locals recommend
Photo of Croteaux Vineyards
Croteaux Vineyards70 locals recommend
Photo of Foster Memorial Beach
Foster Memorial Beach43 locals recommend
Photo of LongHouse Reserve
LongHouse Reserve116 locals recommend
Photo of Parrish Art Museum
Parrish Art Museum264 locals recommend

Other great vacation rentals in The Hamptons

Home in East Hampton
Beautiful and cozy East Hampton Getaway
Individual Host
Guest suite in Hampton Bays
CHARMING OCEAN BUNGALOW
Individual Host
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Home in Water Mill
Designer's Own, w Pool, 5 min. to Ocean & Village
Individual Host
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Rental unit in Sag Harbor
Pet friendly, artists apartment & guest cabin.
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Cottage in Southampton
Charming Southampton Beach Cottage 3 bedroom
Individual Host
Home in Southampton
Dream Home with a wonderful heated pool in SH
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Home in East Hampton
HOT TUB OPEN ALL YR*BOOK NOW SPCL!!!!! *BRAND NEW
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Cottage in Sag Harbor
Steps to the Beach - Designer Cove House Cottage
Individual Host
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Home in East Hampton
East Hampton Village Fringe Escape W/ heated Pool
Individual Host
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Private room in Amagansett
Cheerful 1-bedroom in the heart of Amagansett.
Individual Host
Condo in Sag Harbor
Cute cottage apartment upstairs above store in Sag
Individual Host
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Home in Southampton
Serene 3 Bed 2.5 Bath House w/Heated SaltwaterPool
Individual Host
SUPERHOST

Your guide to The Hamptons

All About The Hamptons

A cluster of towns and hamlets on Long Island’s South Fork, The Hamptons combines long stretches of coastline, pretty villages, and verdant farmland with sought-after restaurants and boutiques. Around a 2.5-hour’ drive from New York City, the popular towns of South Hampton, East Hampton, Sag Harbor, Water Mill, Amagansett, and Bridgehampton are popular trips out of the city for their laid-back vibe, arts scene, and historic charm. The western towns of Montauk, Hamptons Bay, and Westhampton are home to farmers’ markets and delis bursting with local produce.

Montauk boasts the area’s best surfing beaches, hip bars and restaurants, and family-friendly activities like the Montauk Lighthouse. Explore the local area’s art heritage at the Pollock-Krasner House and get a glimpse into the artists’ studios. For something a little more active, rent kayaks, hop on a bike, grab a paddleboard, or set sail for an idyllic afternoon on the waves. Keen windsurfers will want to head to Napeague Bay for the best conditions.


When is the best time to stay in a vacation rental in The Hamptons?

The Hamptons experience warm, humid summers and cold, wet winters. Beachgoers will want to visit houses and cottages in The Hamptons for rent during the summer months — June to September — to make the most of the coastal lifestyle. Those braving the winter, especially January and February, will be rewarded with more space and a free run at the region’s top restaurants and bars, although some businesses close once the summer visitors return home. The Hamptons Restaurant Week takes place each March, and moderate spring temperatures make this an ideal time to explore the outdoors, hike Hither Hills, and visit the many wineries around the sound. Fall brings autumn colors and annual festivals, including the Hamptons International Film Festival and the Oyster Bay Oyster Fest in October.


What are the top things to do in The Hamptons?

Long Island Wine Trail

With over 50 wineries to choose from between the South Fork and the North Fork, you’ll need a few days to get a full taste of what the region has to offer, with a range of grapes, winemaking styles, and tasting rooms. Sample wine while sitting on a cozy patio or meandering through a lush sculpture garden. Most tasting rooms stay open during the off-season, making the Long Island Wine Trail a year-round destination.

Parrish Art Museum in Water Mill

Get inspired by more than 3,000 paintings, works on paper, and mixed media by local artists at the Parrish Art Museum. The In Artists Stories series offers a dynamic history of artists from the 1820s to the present through photographs, biographical information, timeline, and interactive map. Discover and connect with the artists of the East End through over 100 public programs and year-round classes and workshops.

Coopers Beach

Coopers Beach stretches along the shores of the upmarket town of Southampton. Sunbathe on fine, white sand or stroll past the grand mansions that line the dunes. Lifeguards are on duty during the summer months. In winter, the wide shoreline showcases stunning ocean views and rolling grass-flanked dunes.

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