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, (298)
"Loved the balcony view….wrong season for swimming but pool looks inviting"
Windward Shores Ocean Resort
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! "
The price is AU$594
includes taxes & fees
27 Oct - 28 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
9.0 out of 10, Wonderful, (2)
"Perfect location."
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access
The Cooper-Burke House
10.0 out of 10, Exceptional, (27)
"Nice property, conveniently located, great host!"
The Cooper-Burke House
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!"
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (140)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
9.8 out of 10, Exceptional, (16)
"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."
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
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."
Relax in Hampton Bays...
CHARMING APARTMENT WITH SEPARATE ENTRANCE
CHARMING APARTMENT WITH SEPARATE ENTRANCE
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
7.4 out of 10, Good, (3)
"The aptly named Charming East Hampton Cottage was a beautiful oasis with lush gardens and comfortable accommodations. The host was very gracious and friendly and communicated with us as soon as we booked the home. My only regret was that we couldnt stay longer."
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
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."
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (75)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
10.0 out of 10, Exceptional, (101)
"Peaceful and lovely home. Our family of 4 including 2 teens enjoyed the pool and outdoor area. The gameroom was a bonus. Plenty of space, great kitchen and the living room has seating for everyone. Extremely clean with all the amenities. "
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
9.6 out of 10, Exceptional, (7)
"Loved it! "
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
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."
The price is AU$1,996
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
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!"
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!"
Luxurious Amagansett home perched on a hill, amazing views, exceptional...
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (73)
"Enjoyed our time. Thank you "
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$594 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.