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.
Apr 25 – May 2
$650 per night
4.98 out of 5 average rating, 126 reviews
Guest favorite
Cabin in Montauk
Montauk | Tiny Cottage in Private Hither Woods
A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car
Sep 10 – 17
$346 per night
4.96 out of 5 average rating, 422 reviews
Guest favorite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.
Nov 14 – 21
$213 per night
4.88 out of 5 average rating, 308 reviews

Popular amenities for The Hamptons vacation rentals

The Hamptons oceanfront vacation rentals

Guest favorite
Bungalow in Montauk
Montauk Oceanview with Fireplace (2)
Oct 11 – 18
$335 per night
4.91 out of 5 average rating, 519 reviews
Guest favorite
Home in East Hampton
Private beach Historical House with large property
Dec 20 – 27
$475 per night
4.94 out of 5 average rating, 200 reviews
Guest favorite
Guest suite in Sag Harbor
Old World Charm Private Suite with Own Entrance
Nov 19 – 24
$250 per night
4.89 out of 5 average rating, 126 reviews
Guest favorite
Apartment in Milford
Water front studio apartment with fireplace.
Aug 28 – Sep 4
$175 per night
4.97 out of 5 average rating, 505 reviews
Guest favorite
Bungalow in Hampton Bays
Hamptons Waterfront- Great Location!
Aug 4 – 11
$641 per night
5.0 out of 5 average rating, 110 reviews
Guest favorite
Home in Milford
Designer Beach Retreat on Exclusive Cedar Beach
Oct 7 – 14
$273 per night
4.98 out of 5 average rating, 144 reviews
Guest favorite
Home in Shirley
Luxurious Beachfront home on the Bay/Amazing views
Oct 27 – Nov 3
$450 per night
4.98 out of 5 average rating, 177 reviews
Guest favorite
Cottage in Montauk
Montauk Waterfront Cottage
Mar 30 – Apr 6
$386 per night
4.88 out of 5 average rating, 147 reviews
Guest favorite
Guesthouse in Jamesport
Walk to Beautiful Beach in Heart of Wine Country
Nov 6 – 13
$321 per night
4.97 out of 5 average rating, 104 reviews
Guest favorite
Home in Shelter Island
Shelter island retreat
Mar 30 – Apr 6
$405 per night
4.97 out of 5 average rating, 156 reviews
Guest favorite
Home in Montauk
Sea Roost
Dec 6 – 13
$595 per night
4.99 out of 5 average rating, 78 reviews
Superhost
Home in East Hampton
East Hampton By the Bay - Clearwater Beach
Apr 30 – May 7
$684 per night
4.95 out of 5 average rating, 21 reviews

The Hamptons home rentals

Guest favorite
Home in Hampton Bays
Beach House Feel - newly renovated backyard Oasis
Apr 30 – May 7
$360 per night
4.98 out of 5 average rating, 112 reviews
Guest favorite
Home in East Hampton
Silver House: 3BR Home with Private Beach Access
May 16 – 23
$372 per night
4.95 out of 5 average rating, 363 reviews
Guest favorite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
Sep 14 – 21
$533 per night
4.97 out of 5 average rating, 121 reviews
Guest favorite
Home in East Hampton
East Hampton (walking distance to village)
Nov 28 – Dec 5
$607 per night
4.97 out of 5 average rating, 118 reviews
Guest favorite
Home in Southampton
Peaceful Hamptons Cottage
Jun 10 – 17
$334 per night
4.9 out of 5 average rating, 178 reviews
Guest favorite
Home in Southampton
Secluded Southampton Luxury Estate with tennis 288
Nov 18 – 25
$692 per night
4.87 out of 5 average rating, 237 reviews
Guest favorite
Home in Southampton
Contemporary house in the woods.
May 9 – 16
$479 per night
4.98 out of 5 average rating, 111 reviews
Guest favorite
Home in Southampton
Southampton Village Classic Summer Special!
May 5 – 12
$677 per night
4.95 out of 5 average rating, 246 reviews
Guest favorite
Home in East Hampton
Charming Quiet Cottage
Feb 4 – 11
$250 per night
4.91 out of 5 average rating, 142 reviews
Guest favorite
Home in Southampton
Bay View Stunner, Modern 6 Bedroom w Heated Pool
Apr 10 – 17
$293 per night
5.0 out of 5 average rating, 36 reviews
Guest favorite
Home in Southampton
Perfect Lake Cottage weekend Hamptons special
Jan 18 – 25
$696 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Sag Harbor
Modern Home in Sag Harbor, NY
May 16 – 23
$681 per night
4.84 out of 5 average rating, 45 reviews

The Hamptons condominium rentals

Guest favorite
Condo in Montauk
Montauk Waterfront Condo w/ Sunset Views
Sep 18 – 25
$417 per night
4.99 out of 5 average rating, 175 reviews
Guest favorite
Condo in Montauk
Deluxe Studio Apt@The Montauk Manor
Dec 19 – 26
$179 per night
4.95 out of 5 average rating, 106 reviews
Superhost
Condo in Montauk
Montauk Royal Atlantic Beach Resort North
Aug 12 – 19
$450 per night
4.8 out of 5 average rating, 227 reviews
Guest favorite
Condo in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
Apr 1 – 8
$205 per night
4.91 out of 5 average rating, 107 reviews
Guest favorite
Condo in Greenport
Beautiful Waterview Condo on the North Fork of LI
Apr 9 – 16
$276 per night
4.93 out of 5 average rating, 120 reviews
Guest favorite
Condo in Greenport
Sound front condominium
Sep 2 – 9
$494 per night
4.83 out of 5 average rating, 141 reviews
Guest favorite
Condo in Montauk
Coastline View Studio
Sep 15 – 22
$999 per night
4.82 out of 5 average rating, 158 reviews
Guest favorite
Condo in Montauk
Renovated Beachfront Condo With An Incredible View
Sep 17 – 24
$699 per night
5.0 out of 5 average rating, 61 reviews
Superhost
Condo in Bridgehampton
Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Sep 6 – 13
$526 per night
4.92 out of 5 average rating, 13 reviews
Guest favorite
Condo in Montauk
Beautiful Condo on the Ocean Bluffs
Apr 23 – 30
$232 per night
4.82 out of 5 average rating, 87 reviews
Superhost
Condo in Montauk
Newly Renovated One Bedroom One Bathroom Suite Jus
May 20 – 27
$349 per night
4.78 out of 5 average rating, 23 reviews
Guest favorite
Condo in Greenport
"Breathtaking Waterfront Water's Edge view"
May 16 – 23
$483 per night
5.0 out of 5 average rating, 90 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.

Frequently Asked Questions

  • How is the weather in The Hamptons?

    The Hamptons has a temperate climate. Summers are warm, with highs around 80°F (27°C), while winters are cooler, with temperatures averaging 38°F (3°C). Spring and fall are generally mild. Remember to pack your swimsuit for the summer, and a cozy jacket for cooler evenings.

  • What is the best time of year to visit The Hamptons?

    The Hamptons is most popular in the summer, from Memorial Day to Labor Day. This is when you can enjoy events like the Hampton Classic Horse Show, the East Hampton Artists & Writers Charity Softball Game, and the Southampton August Fair.

  • What are the best places to stay in The Hamptons?

    Popular areas to stay in The Hamptons include the vibrant towns of Southampton and East Hampton. For those seeking a more laid-back vibe, Montauk and Amagansett are often recommended. If you're looking for a mix of both, consider staying in the charming village of Sag Harbor.

  • What are the best places to visit in The Hamptons?

    In The Hamptons, you might enjoy visiting the historic Montauk Point Lighthouse, the serene LongHouse Reserve, or the iconic Maidstone Club. You could also explore the Parrish Art Museum or take a leisurely stroll around the beautiful Elizabeth A. Morton National Wildlife Refuge.

  • What are some hiking trails in The Hamptons?

    The Hamptons is home to several hiking trails. The Hither Hills State Park trail, the Mashomack Preserve trails on Shelter Island, and the Walking Dunes trail in Napeague are all frequently suggested. These provide opportunities to explore the beautiful natural scenery of The Hamptons.

  • What are some family activities to do in The Hamptons?

    Families often enjoy visiting the Children's Museum of the East End, exploring the Montauk Point Lighthouse, or spending a day at Cooper's Beach. You might also consider taking a stroll around the Southampton Arts Center or exploring the fascinating exhibits at the South Fork Natural History Museum.

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