Hamptons Holiday Rentals

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Holiday Rentals in Hamptons

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (300)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
Windward Shores Ocean Resort
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
10.0 out of 10, Exceptional, (192)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
United States
Eva L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
9.0 out of 10, Wonderful, (2)
"Perfect location."
United States
Devin O.
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
United States
James S.
The price is AU$580
includes taxes & fees
28 Oct - 29 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (141)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Relax in Hampton Bays...
9.8 out of 10, Exceptional, (76)
"We stayed for a weekend while out east for a wedding. The property was lovely and exactly as pictured."
United States
Jennifer P.
Relax in Hampton Bays...
CHARMING APARTMENT WITH SEPARATE ENTRANCE
CHARMING APARTMENT WITH SEPARATE ENTRANCE
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
8.0 out of 10, Very good, (4)
"Great place to stay with family! The terrace was beautiful. The property felt private and safe. 10/10!"
United States
Ashley N.
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."
United States
Patricia Fox M.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
United States
Katie C.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
10.0 out of 10, Exceptional, (91)
"The house was exactly as described, with lots of space and fully stocked. The pool was amazing. The location was perfect and within walking distance of Westhampton Beach. Colleen was an excellent host and extremely communicative throughout our stay. Highly recommend :)"
United States
Max S.
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
9.8 out of 10, Exceptional, (17)
"Had an amazing stay here and would definitely recommend to others!! Only issue was the heat did not work in certain areas. House and backyard / pool area was spacious and beautiful. Perfect for large groups. Would definitely stay again."
United States
shelby h.
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
9.6 out of 10, Exceptional, (7)
"Loved it! "
United States
debra sue k.
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊
9.4 out of 10, Exceptional, (53)
"Great house, great location, excellent host"
United States
Daniel E.
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊
Private Bridgehampton home with Pool.
10.0 out of 10, Exceptional, (4)
"The house and property were so nice. We have a 10 and 11 year old. They played outside or were swimming in the pool the entire time. It's close to great shopping and beaches. It was a very relaxing and enjoyable long weekend. Everything was perfect!"
United States
Heather M.
Private Bridgehampton home with Pool.
Luxurious Amagansett home perched on a hill, amazing views, exceptional...
10.0 out of 10, Exceptional, (2)
"Thanks for a great stay on Cliff Road!"
United States
G C.
Luxurious Amagansett home perched on a hill, amazing views, exceptional...
Location: Beautiful Farm House, Walk to Shops, Walk to Beach & Walk from Jitney!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful classic farmhouse with all the modern amenities including high speed internet, great kitchen and brand new heating/AC so you can enjoy all the comforts of a 5 Star Resort. Conveniently located within walking distance to the Palm, Movie Theatre and the bus stop to NYC. Beverly Leopold was a very conscientious and hospitable host. Highly recommend!"
United States
TODD T.
Location: Beautiful Farm House, Walk to Shops, Walk to Beach & Walk from Jitney!
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (73)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hamptons Hotel Reviews

Find out more about Hamptons

Everything you need to know about Hamptons holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hamptons holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hamptons holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hamptons holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hamptons. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hamptons holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hamptons holiday rentals we have selected for you start as low as AU$580 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hamptons rentals

At Expedia, we put the best Hamptons holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hamptons rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hamptons holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hamptons. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.