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20 of the Best Hamptons Summer Rentals to Book ASAP

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VRBO

There are few things quite as luxurious as a beachy summer getaway, and the Hamptons is perhaps the best place of all to soak up the sun in style (according to New Yorkers, at least). Which is precisely why we tracked down 20 of the best Hamptons rummer rentals to inspire a weekend, or week-long, vacation for you and your crew. Let us tell you, between Airbnb, VRBO, Plum Guide and more rental sites, there is a lot to choose from.

There are sprawling properties perfect for large families (like this Southhampton stunner that sleeps 12) and cozy houses better suited for smaller friend groups (check out this Sag Harbor Airbnb gem before it books up). And while there are absolutely some splurge-worthy share houses well worth the dough (ahem, this Southampton house listed on VRBO is truly jaw-dropping), we made sure to include multiple options that are decidedly more budget-friendly. Now, without further ado, here are 20 of the best Hamptons summer rentals you’ll want to book ASAP.

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The Best Hamptons Summer Rentals at a Glance

1

Most Spacious

Water Mill Lofty Beach Barn, Water Mill

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2

Unique Design

Mid-Century Modern, East Hampton

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3

Best for Throwing a Summer Bash

Stunning Hampton Holiday Home, East Hampton

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4

Best Family-Friendly

Southampton Private Getaway, Southampton

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5

Best Hygge Vibes

Spacious Woodsy Getaway, East Hampton

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  • Guests: Sleeps 8
  • Price: $916/night on avergage
  • Getting there: 2 hours and 15 minutes from NYC

Only 3.5 miles from the beach, this sprawling property is an easy choice for anyone looking to get away from the city. Sitting on 3,000 square feet, the home has an open plan with a large separate den, which is an amazing spot for the kids or large groups to spread out and enjoy a movie, books or games. And if you ever get tired of splashing in the pool, you can easily head to either Cooper's Beach or Flying Point Beach which are both less than a ten-minute drive away.

  • Guests: Sleeps 8
  • Price: $679/night on average
  • Getting there: 2 hours and 56 minutes from NYC

This house is definitely the one for any design and architecture savvy New Yorkers. We live for a mid-century modern look and this gorgeous, deep navy blue and wood accented beach house, designed by famed architect Carl Koch, hits all the marks. It’s got gorgeous geometric lines, large windows and glass sliding doors to let in lots of light. The living room (with a fireplace), kitchen and bedrooms are spacious and airy, so you and your crew won’t feel squeezed in at all. If you don’t feel like hanging out on the expansive wraparound deck with a hammock, lounge by the pool surrounded by teak chairs. After a day of relaxing, take a short walk down the path to arrive to your own private beach at Lion Head Bay to enjoy a Hampton’s sunset.

Best for Throwing a Summer Bash

3. Stunning Hampton Holiday Home, East Hampton

VRBO

  • Guests: Sleeps 10
  • Price: $1,542/night on average
  • Getting there: 2 hours and 56 minutes from Manhattan

Got a birthday, anniversary or another special event coming up? This East Hampton beauty is the perfect place to host all kinds of festivities. This stunning and roomy beach house keeps it simple and chic with a white, slate grey and blue palette throughout the home. It also has massive ceilings to house a movie screening room, billiards table, gym and game room. Plus, it comes with spa-level amenities—sauna, outdoor heated pool and steam shower—to really help you unwind after your blowout bash.

Best Family-Friendly

4. Southampton Private Getaway, Southampton

VRBO

  • Guests: Sleeps 12
  • Price: $710/night on average
  • Getting there: 2 hours and 14 minutes from NYC

This five-bedroom home looks like something straight out of an interior design magazine. The affordable-ish (by Hamptons standards, that is) yet gorgeous find is ideal for families thanks to the game-filled living room, big backyard and open kitchen. It also boasts a private community beach, a saltwater pool and both tennis and basketball courts. And if you want some activities outside your gorgeous rental, the house is closely located to apple or pumpkin picking as well as multiple vineyards.

  • Guests: Sleeps 12
  • Price: $1,586/night on average
  • Getting there: 2 hours and 41 minutes from NYC

Modern Alpine ski-chalet vibes, but make it Hamptons. We took one look at this open-floor plan format place and were itching to book it. It’s got this Scandinavian feel that makes it feel so hygge chic no matter the time of the year. There’s also a souped-up chef’s kitchen, huge outdoor pool, clawfoot bathtub and five bedrooms over three floors. It’s situated right near East Hampton Village, Sag Harbor and Wainscott Beach, giving you plenty of options for easy exploration.

Best for Friend Groups

6. Stylish Artist’s Home, East Hampton

Airbnb

  • Guests: Sleeps 8
  • Price: $650/night on average
  • Getting there: 3 hours from NYC

Grab your friends and head to this summer house that offers quick access to beaches, dining and activities in nearby East Hampton, Sag Harbor, Bridgehampton and Wainscott (so many options!). Homebodies and introverts alike will love this hidden, comfortable home with its inground pool, entertaining deck, fire pit, grill and outdoor shower. And the trendy interior design is great for snapping photos of indoor hangs whether you’re chilling by the wood-burning fireplace, chic dining room or cozy couches in the open living room.

Best Beachside Lodging

7. Beach House, Montauk

Airbnb

  • Guests: Sleeps 10
  • Price: $821/night on average
  • Getting there: 3 hours and 35 minutes from NYC

With unobstructed views of the ocean, this beautiful home is located right off Montauk Highway meaning it’s also walking distance from the village center. Bikes are also provided for guests who want a quicker way to get into town. Use the private path to head to the beach where you can spend the day on the sand or to cozy up and watch the sunset. Guests can also use the house’s firepit and outdoor grill for dining al fresco. Overall, this place sounds like a relaxing dream, perfect for beach-lovers.

Best Affordable

8. Village Property, Southampton

Airbnb

  • Guests: Sleeps 11
  • Price: $538/night on average
  • Getting there: 2 hours and 20 minutes from NYC

We’ll be honest, the Hamptons are not the most affordable of vacation destinations. But that doesn’t mean you can’t find some hidden deals if you look—case in point, this homey and accommodating house located in the village of Southampton. Its centralized location makes it ideal for groups who want to explore the surrounding areas and experience the nearby shops, bars and restaurants. No car? No problem. The property is within walking distance of the train station and Jitney stop. There’s also a large deck that overlooks an inground pool and a fenced in yard where plenty of outdoor games can be played.

Best Little-Known Beach

9. The Captain’s House, South Jamesport

Plum Guide

  • Guests: Sleeps 10
  • Price: $984/night on average
  • Getting there: 2 hours, 15 minutes from NYC

Located on the North Fork of Long Island, South Jamesport is not nearly as crowded as the Hamptons proper, but is every bit as charming, with beaches all along Peconic Bay. And this incredibly well-appointed home is just steps from the beach, with room for ten guests. There’s an open-concept kitchen that has everything you need to cook up whatever you might be craving, and is perfectly designed for entertaining. Guests are required to book at least three nights, but we suspect you’ll be wishing you booked more after touring those Scandinavian-inpired bedrooms.

Best Homey Vibes

10. Island View House, Sag Harbor

Airbnb

  • Guests: Sleeps 12
  • Price: $346/night on average
  • Getting there: 2 hours and 40 minutes from NYC

The modern cozy vibes of this Sag Harbor house are sure to make you feel instantly at ease so you can start relaxing right away. Although it sleeps 12 and has a layout that’s great for large groups, the listing specifically will not accommodate bachelor or bachelorette parties. That said, big families or chill gatherings can enjoy a saltwater pool, hot tub, blooming garden and outdoor lounge that surrounds a wood-burning fire pit. The house also boasts hotel-quality bedding, a formal dining room and a full chef’s kitchen. Southampton and East Hampton are about a 20-minute drive away and just 40 minutes to Montauk. Hikers will appreciate a footpath to a hiking trail that can be found at the top of the street.

Best for Ocean Views

11. Beachfront House, Montauk

Airbnb

  • Guests: Sleeps 10
  • Price: $879/night on average
  • Getting there: 3 hours and 30 minutes from NYC

This Montauk beach house is all about the panoramic water views. The balcony and porch overlook a quiet local beach that’s also just a half hour from the center of town, making it easy to chill by the water all afternoon before strolling into town to hit up the local bars and restaurants for the evening. The airy, open floor plan has quintessential beach-house vibes, and guests have access to an outdoor grill and modern kitchen.

Best for Couples

12. Artist’s Retreat, Sagaponack

VRBO

  • Guests: Sleeps 3
  • Price: $240/night on average
  • Getting there: 2 hours, 30 minutes from NYC

Technically this cozy-yet-modern home has room for three, but we think it’s really the ideal spot for a duo looking to getaway for a romantic weekend. It’s also pet-friendly, so you can bring your pup or kitty along for the ride. And although it is within a ten minute drive from the beach, numerous vineyards and multiple golf courses, the true charm of this petite house is its privacy and seclusion. Although it shares a driveway with the main house, guests have full and private access to the pool and outdoor amenities.

Best Minimalist Design

13. The Little Sparrow, Shinnecock Hills

Plum Guide

  • Guests: Sleeps 6
  • Price: $849/night on average
  • Getting there: 2 hours, 15 minutes from NYC

This three-bedroom home is a minimalist’s dream, ideal for anyone looking to truly escape the clutter and bustle of the city. But don’t let that chic simplicity trick you into thinking there aren’t also amenities aplenty. The kitchen has three different coffee makers (a drip maker, an espresso machine and a pod machine) and there is a full DVD library, as well as a pool table to keep you entertained. Of course, the real draw is the fenced-in pool with comfy lounge chairs and a view of the surround treetops and a garden just below.

Best for Interior Design Buffs

14. Light-Filled Village Gem, Sag Harbor

airbnb

  • Guests: Sleeps 6
  • Price: $1,500/night on average
  • Getting there: 2 hours and 20 minutes from NYC

It’s no surprise that this house was featured on Homes & Gardens with its sprawling grounds and unique construction. The 20-foot floor-to-ceiling windows and skylights throughout the home bring in tons of natural light and lend a homey vibe to the space.  The first floor includes a glass dining room, gourmet kitchen and oversized mahogany deck that looks out onto the yard. Guests can use the inground pool, grill and outdoor space in the summertime and the fireplace, lounge and Scandinavian sauna in the colder months.

Best Secluded Getaway

15. Private Hamptons Escape, Amagansett

airbnb

  • Guests: Sleeps 12
  • Price: $1,800/night on average
  • Getting there: 2 hours and 30 minutes from NYC

Sneak away from the hustle and bustle of your everyday life and spend your summer days at this private and luxurious home in Amagansett. Everything you need is already situated on the property including a home office, backyard fire pit, game room, Peloton bike, home theater, chef’s kitchen, hot tub, patio and inground pool. Rain or shine, you’ll be able to enjoy everything this home has to offer without needing to wander into town or to the beach, both of which are conveniently located less than two miles away, should you find yourself wanting.

Best for Small Groups

16. Open Concept Home, Bridgehampton

airbnb

  • Guests: Sleeps 6
  • Price: $300/night on average
  • Getting there: 2 hours from NYC

This Bridgehampton home is great for folks who want to see it all and is located smack dab in the middle of multiple beaches, wineries, farms and gourmet restaurants. It’s also easily accessible via train or Jitney. The home provides bikes for those who want to maximize exploring the surrounding area, but if staying in is more your style, there’s so much to do right at home. Enjoy a large eat-in kitchen, fire pit, back deck, private backyard and heated pool.

Best for Surfers

17. Ditch House, Montauk

airbnb

  • Guests: Sleeps 8
  • Price: $2,143/night on average
  • Getting there: 3 hours from NYC

Surfers and beach lovers alike will appreciate this newly renovated house just steps away from the famous Ditch Plains Beach. With a lush backyard and sprawling ocean views, this house is perfect for a group looking to maximize their rest and relaxation. Guests can chill out and unwind after a long day on the sand at the home’s outdoor dining area equipped with a fire pit and barbeques.

Best for Active Travelers

18. Hampton Oasis, Westhampton Beach

airbnb

  • Guests: Sleeps 12
  • Price: $447/night on average
  • Getting there: 2 hours and 45 minutes from NYC

This delightful Westhampton Beach home is just a six-minute drive to the beach and walking distance from the center of town. As for activities, you’d be hard pressed to find a rental with more options. This house has board games, beach accessories, gym equipment and tons of cooking tools for whipping up experimental dishes or beloved favorites. Don’t forget the outdoor oasis where guests can swim, lounge and grill all in one place.

Best for Relaxing without the Kids

19. She’s a Blues Peconic Bay Hideaway, Southampton

Plum Guide

  • Guests: Sleeps 6
  • Price: $1,497/night on average
  • Getting there: 2 hours, 30 minutes from NYC

A working wood fireplace, a views of Peconic Bay, an outdoor dining table, a tree-lined pool—these are just a few of the treats you can expect at this adorable Southampton stay. The inside has high ceilings, plenty of natural light and airy shared spaces for you and your friends or family to convene. Take a dip in the freshwater pool, or there’s a private bay beach just a short walk away. And while the house is pet-friendly, it is not recommended for small children, which may just be the perfect excuse for you and your partner to book a relaxing adults-only getaway.

Best Pool

20. Family Home, Sagaponack

VRBO

  • Guests: Sleeps 8
  • Price: $540/night on average
  • Getting there: 2 hours, 30 minutes from NYC

Another pet-friendly option, this four-bedroom cottage is reportedly every bit as darling as the pictures suggest. There is a pool out back with teak lounge chairs for relaxing after a dip, as well as an outdoor dining table for meals al fresco. It’s just a short drive from the beach or Poxabogue County Park, a beautiful preserve full of wildlife with stunning views. Even better, the house is within walking distance of Loaves & Fishes, home of the best scones in the Hamptons. (P.S. There’s an additional bedroom in the pool house should you need more space to spread out.)


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