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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
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.
Oct 16 – 23
G$68,477 GYD per night
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 4 – 11
G$136,189 GYD per night
Guest favorite
Guesthouse in Southampton
Tiny Home in Prime Spot in Southampton Village
Located in the heart of Southampton Village, this intimate, centrally-located cottage is the ideal getaway. Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!
Jun 26 – Jul 3
G$81,637 GYD per night

Popular amenities for The Hamptons vacation rentals

The Hamptons beach vacation rentals

Guest favorite
Guesthouse in Hampton Bays
WELCOME TO THE LOVE SHACK BY THE SEA
Oct 23 – 30
G$104,760 GYD per night
Guest favorite
Home in East Hampton
Silver House: 3BR Home with Private Beach Access
Mar 7 – 14
G$41,964 GYD per night
Guest favorite
Home in Hampton Bays
Beach House Feel - newly renovated backyard Oasis
Sep 21 – 28
G$144,120 GYD per night
Guest favorite
Guest suite in Stonington
Morgan Suite
Jul 21 – 28
G$41,737 GYD per night
Guest favorite
Apartment in Milford
Water front studio apartment with fireplace.
Apr 11 – 18
G$31,705 GYD per night
Guest favorite
Guest suite in East Hampton
Private Cozy Cottage with Pool / Private Beach
Apr 9 – 16
G$49,028 GYD per night
Guest favorite
Home in East Hampton
Private beach Historical House with large property
Jul 7 – 14
G$169,188 GYD per night
Guest favorite
Home in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
May 3 – 10
G$67,117 GYD per night
Guest favorite
Bungalow in Montauk
Montauk Oceanview with Fireplace (2)
Sep 5 – 12
G$78,570 GYD per night
Guest favorite
Home in Southampton
PICTURE PERFECT SOUTHAMPTON HOME-
Jul 4 – 11
G$157,141 GYD per night
Superhost
Home in Port Jefferson
The Hidden Retreat ~ Family friendly Walk to Beach
Mar 2 – 9
G$79,468 GYD per night
Guest favorite
Guest suite in Sag Harbor
Artists Sag Harbor Village Retreat
Aug 22 – 29
G$66,785 GYD per night

Home rentals in The Hamptons

Guest favorite
Home in East Hampton
1800 Historical East Hampton Home, 1 Mile to Town!
Apr 26 – May 3
G$110,747 GYD per night
Guest favorite
Home in Sag Harbor
Luxury Private King Suite + 2 Floor Living Space
Aug 2 – 9
G$103,713 GYD per night
Guest favorite
Home in Sag Harbor
Sag Harbor home away from home
Oct 15 – 22
G$78,241 GYD per night
Guest favorite
Home in East Hampton
East Hampton (walking distance to village)
Sep 15 – 22
G$128,203 GYD per night
Guest favorite
Home in East Hampton
Explore the Water & Woods at a Relaxing Retreat
Apr 5 – 12
G$111,778 GYD per night
Guest favorite
Home in Lyme
“The Answer” Tidal River-Kayaks Fire pit Fireplace
Apr 19 – 26
G$50,016 GYD per night
Guest favorite
Home in Shirley
Luxurious Beachfront home on the Bay/Amazing views
Jan 10 – 17
G$94,284 GYD per night
Guest favorite
Home in Southampton
Peaceful Hamptons Cottage
Apr 1 – 8
G$49,790 GYD per night
Guest favorite
Home in Manorville
Ultimate House with Heated Pool, Hot Tub and Sauna
Mar 1 – 8
G$53,422 GYD per night
Guest favorite
Home in Southampton
Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
Jan 19 – 26
G$133,570 GYD per night
Guest favorite
Home in Montauk
House on Napeague Harbor, Amagansett
Jun 7 – 14
G$171,734 GYD per night
Guest favorite
Home in East Hampton
East Hampton Village Fringe, Renovated with Pool
Apr 3 – 10
G$45,646 GYD per night

Cottage rentals in The Hamptons

Guest favorite
Cottage in Southampton
Secluded Southampton Cottage w/Pool & Spa
Oct 17 – 24
G$80,896 GYD per night
Guest favorite
Cottage in East Hampton
Carriage House - Cottage in East Hampton Village
Dec 13 – 20
G$56,382 GYD per night
Guest favorite
Cottage in East Hampton
East Hampton Fisherman’s Cottage with Secret Room
Feb 8 – 15
G$51,856 GYD per night
Guest favorite
Cottage in Montauk
Waterfront Cottage, Fort Pond MTK
Sep 17 – 24
G$107,694 GYD per night
Guest favorite
Cottage in Montauk
Laid-Back Surf Shack steps to beach & downtown!
Jan 22 – 29
G$94,284 GYD per night
Guest favorite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
Jan 31 – Feb 7
G$38,552 GYD per night
Guest favorite
Cottage in Patchogue
Quaint Cottage on Long Island's South Shore.
Apr 11 – 18
G$26,651 GYD per night
Guest favorite
Cottage in Westhampton Beach
Cool Tiny Cottage Artist Loft!
Oct 10 – 17
G$37,525 GYD per night
Guest favorite
Cottage in Clinton
Shalom Cottage with beach rights.
Dec 8 – 15
G$18,399 GYD per night
Guest favorite
Cottage in East Lyme
Your Nest Near The Beach
Mar 20 – 27
G$35,110 GYD per night
Guest favorite
Cottage in Hampton Bays
Hamptons cottage just steps from the beach.
Apr 26 – May 3
G$78,570 GYD per night
Superhost
Cottage in Charlestown
Pet-Friendly Private Beach Oceanfront Cottage A/C
Dec 9 – 16
G$69,914 GYD per night

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.

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