Hamptons Holiday Rentals

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Holiday Rentals in Hamptons

Windward Shores Ocean Resort

3.0 star property
Amagansett
8.8 out of 10, Excellent, (303)
"Easy checking in and out Easy access few steps to beach from first floor unit "
United States
comenius
Windward Shores Ocean Resort

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Westhampton Beach
10.0 out of 10, Exceptional, (194)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah 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

Beach Hampton
9.0 out of 10, Wonderful, (2)
"This worked out very well for our family. We loved being close to the beautiful beach, and the house is clean and cute. It's an upside down house, with living areas accessible by an open spiral staircase but we were able to block that off from our toddler. The owner was easy to communicate with and very accommodating. "
United States
Anne S.
Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
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

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
9.6 out of 10, Exceptional, (142)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Southampton
9.8 out of 10, Exceptional, (17)
"This House was fantastic for a our friends weekend get away. Tara at StayMarquis was incredibly welcoming and helpful, the space was clean and comfortable, and the location was perfect to walk in to town. The property itself was beautifully decorated and cozy. We would definitely stay here again. Can wait to book another stay with StayMarquis."
United States
Kathleen
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Relax in Hampton Bays...

Hampton Bays
9.8 out of 10, Exceptional, (76)
" Very clean a little dated but excellent location"
United States
Regina J.
Relax in Hampton Bays...

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

East Hampton
8.0 out of 10, Very good, (4)
"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."
United States
Lisa R.
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton
10.0 out of 10, Exceptional, (95)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
United States
colin f.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Southampton
9.8 out of 10, Exceptional, (55)
"We had a great time together at Daniels home. Plenty of room for all of us and the playroom was a huge hit with the little kids. Daniel was very responsive and gave us a tour of the neighborhood when we got there which we greatly appreciated. Overall the week was memorable for all of us!"
United States
Beth B.
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton
10.0 out of 10, Exceptional, (13)
"House was immaculate and perfect for our family of 5"
United States
mark h.
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Hampton Bays
10.0 out of 10, Exceptional, (12)
"This is a simple house with a great view right on the water. The beds and bedding were comfortable. Despite being on the water, it has a nice yard and little beach area. "
United States
Coleman H.
The price is NZ$2,378
includes taxes & fees
12 Nov - 13 Nov
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Canoe Place Waterfront Residences

4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is NZ$4,297
includes taxes & fees
24 Nov - 25 Nov
Canoe Place Waterfront Residences

🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

Westhampton Beach
9.4 out of 10, Exceptional, (55)
"Great house, great location, excellent host"
United States
Daniel E.
🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

Central Private Bridgehampton home

Sag Harbor
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.
Central Private Bridgehampton home

Location: Beautiful Farm House, Walk to Shops, Walk to Beach & Walk from Jitney!

2.0 star property
East Hampton
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!

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Hampton Bays
9.8 out of 10, Exceptional, (19)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
United States
Angela G.
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Minutes from the beach, brand new 4 bedroom

Southampton
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is NZ$1,966
includes taxes & fees
13 Nov - 14 Nov
Minutes from the beach, brand new 4 bedroom

Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

Westhampton Beach
10.0 out of 10, Exceptional, (91)
"Great fun for all and very appreciative of the outside space for children to play. It easily accommodated our family of fourteen and offered privacy for all. Thank you for sharing your home with us. MAS"
United States
Frank S.
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
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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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 favorite 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 depends 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 NZ$801 per night. Entering your travel dates in the search wizard you might find 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.