The Hamptons vacation rentals

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Top-rated vacation rentals in The Hamptons

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

Guest favorite
Cottage in Riverhead
Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.
Dec 10 – 17
$650 per night
4.98 out of 5 average rating, 126 reviews
Guest favorite
Guest suite in Hampton Bays
CHARMING OCEAN BUNGALOW
My ocean Bungalow is super well located in Hampton Bays. You will be 10 minutes away from the center of town where the Hampton Bays train station is. You also have Starbucks, Ride Aid, king Kullen, and great eateries at your fingertips. You will also have another two great supermarkets; Stop&Shop and Wild by Nature natural food store. You will be staying in a room with a feeling of a Junior Suite with approximately 400sq feet, a much larger area than a standard room. It has an attached small full bathroom, a living space that I call “home theater” with a 75” smart TV, a wet Bar with Coffee, Expresso and Tea, your own refrigerator. No heavy cooking is allowed indoors but I will offer a grill outside, for the most gastronomically inclined guests ... there’s no dining area but you are more welcome to use the dining table at the outdoor stone patio. One of the nicest thing about our location is that we are 5 minutes from Ponquogue Beach with excellent near by restaurants such as Oklands, Sundays on the Bay, on Beach Road and Dockers waterside on Dune Road. Meschutt beach is also a great location with live music throughout the summer, not a beach for surfers or adventure swimmers, since it’s on Peconic Bay, but on a plus side, there’s a full outdoor bar for adults, I love their Rum punch, and a full service snack bar, and a gift shop that sells beach gear... etc.
Apr 16 – 23
$125 per night
4.98 out of 5 average rating, 308 reviews
Guest favorite
Guesthouse in Hampton Bays
WELCOME TO THE LOVE SHACK BY THE SEA
Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.
Oct 29 – Nov 5
$500 per night
4.96 out of 5 average rating, 145 reviews

Popular amenities for The Hamptons vacation rentals

The Hamptons beach vacation rentals

Guest favorite
Apartment in Southampton
Sunny Southampton Studio
Apr 16 – 23
$120 per night
4.96 out of 5 average rating, 156 reviews
Guest favorite
Home in Montauk
DITCH PLAINS SURF HOUSE
Nov 21 – 28
$294 per night
4.9 out of 5 average rating, 408 reviews
Guest favorite
Home in Southampton
PICTURE PERFECT SOUTHAMPTON HOME-
Jun 10 – 17
$500 per night
4.9 out of 5 average rating, 205 reviews
Guest favorite
Cottage in Montauk
Montauk Oceanview Studio 6
Mar 7 – 14
$138 per night
4.92 out of 5 average rating, 204 reviews
Guest favorite
Cottage in Montauk
Waterfront Cottage, Fort Pond MTK
Oct 15 – 22
$456 per night
4.87 out of 5 average rating, 216 reviews
Guest favorite
Guest suite in East Hampton
Private Cozy Cottage with Pool / Private Beach
Apr 22 – 29
$234 per night
4.89 out of 5 average rating, 222 reviews
Guest favorite
Home in East Hampton
Silver House: 3BR Home with Private Beach Access
May 1 – 8
$289 per night
4.95 out of 5 average rating, 358 reviews
Guest favorite
Home in Hampton Bays
Beach House Feel - newly renovated backyard Oasis
Apr 24 – May 1
$360 per night
4.98 out of 5 average rating, 112 reviews
Guest favorite
Home in East Hampton
Private beach Historical House with large property
Feb 4 – 11
$475 per night
4.94 out of 5 average rating, 199 reviews
Guest favorite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
Aug 23 – 30
$319 per night
4.88 out of 5 average rating, 307 reviews
Guest favorite
Home in Southampton
Secluded Southampton Luxury Estate. 286
Nov 9 – 16
$692 per night
4.88 out of 5 average rating, 192 reviews
Guest favorite
Apartment in Hampton Bays
Private & Cozy Cottage with short walk to beach!
Jan 31 – Feb 7
$248 per night
4.97 out of 5 average rating, 340 reviews

Home rentals in The Hamptons

Guest favorite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
Oct 27 – Nov 3
$370 per night
4.97 out of 5 average rating, 120 reviews
Guest favorite
Home in East Hampton
1800 Historical East Hampton Home, 1 Mile to Town!
May 2 – 9
$686 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Home in East Hampton
Fantastic East Hampton Village home with Pool
Apr 2 – 9
$171 per night
4.91 out of 5 average rating, 122 reviews
Guest favorite
Home in Sag Harbor
Luxury Private King Suite + 2 Floor Living Space
May 13 – 20
$387 per night
4.95 out of 5 average rating, 129 reviews
Guest favorite
Home in Sag Harbor
Sag Harbor home away from home
Dec 26 – Jan 2
$381 per night
4.97 out of 5 average rating, 169 reviews
Guest favorite
Home in East Hampton
Explore the Water & Woods at a Relaxing Retreat
Nov 2 – 9
$794 per night
4.97 out of 5 average rating, 112 reviews
Guest favorite
Home in East Hampton
East Hampton (walking distance to village)
Oct 9 – 16
$617 per night
4.97 out of 5 average rating, 118 reviews
Guest favorite
Home in Southampton
Peaceful Hamptons Cottage
Mar 20 – 27
$237 per night
4.9 out of 5 average rating, 178 reviews
Guest favorite
Home in Southampton
Waterview DogsStayFree! Kayaks Fireplace Ping-Pong
Mar 5 – 12
$240 per night
4.96 out of 5 average rating, 128 reviews
Guest favorite
Home in Center Moriches
Walk to beach and playground. Outdoor hot tub.
Mar 4 – 11
$227 per night
4.98 out of 5 average rating, 185 reviews
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
Jan 2 – 9
$541 per night
4.97 out of 5 average rating, 183 reviews
Guest favorite
Home in Shirley
Luxurious Beachfront home on the Bay/Amazing views
Jan 16 – 23
$450 per night
4.99 out of 5 average rating, 175 reviews

Cottage rentals in The Hamptons

Guest favorite
Cottage in East Hampton
Carriage House - Cottage in East Hampton Village
Feb 21 – 28
$269 per night
4.98 out of 5 average rating, 258 reviews
Guest favorite
Cottage in Montauk
Laid-Back Surf Shack steps to beach & downtown!
Jan 12 – 19
$450 per night
4.87 out of 5 average rating, 173 reviews
Guest favorite
Cottage in East Hampton
East Hampton Fisherman’s Cottage with Secret Room
Feb 19 – 26
$248 per night
4.89 out of 5 average rating, 120 reviews
Guest favorite
Cottage in Patchogue
Quaint Cottage on Long Island's South Shore.
Mar 23 – 30
$127 per night
4.94 out of 5 average rating, 196 reviews
Guest favorite
Cottage in Westhampton Beach
Cool Tiny Cottage Artist Loft!
Dec 17 – 24
$179 per night
4.93 out of 5 average rating, 147 reviews
Guest favorite
Cottage in East Lyme
Your Nest Near The Beach
Jun 7 – 14
$191 per night
4.97 out of 5 average rating, 230 reviews
Guest favorite
Cottage in Hampton Bays
Hamptons cottage just steps from the beach.
Mar 12 – 19
$375 per night
4.9 out of 5 average rating, 109 reviews
Superhost
Cottage in Old Lyme
Private Beach Cottage
Apr 13 – 20
$110 per night
4.81 out of 5 average rating, 163 reviews
Superhost
Cottage in Branford
Cozy Home In Short Beach Community
Mar 6 – 13
$119 per night
4.85 out of 5 average rating, 193 reviews
Guest favorite
Cottage in Groton
Restored Historic Schoolhouse, Mystic River Views
Feb 3 – 10
$127 per night
4.95 out of 5 average rating, 265 reviews
Guest favorite
Cottage in Waterford
Classic CT Cottage w/ Trail by Harkness Park/Ocean
Mar 26 – Apr 2
$141 per night
4.99 out of 5 average rating, 102 reviews
Guest favorite
Cottage in Clinton
Shalom Cottage with beach rights.
Apr 10 – 17
$107 per night
4.87 out of 5 average rating, 385 reviews

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.


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.


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.

Destinations to explore

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