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Top Holiday Rentals in Hamptons

Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (237)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is £233
includes taxes & fees
3 Jun - 4 Jun
Windward Shores Ocean Resort
Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (47)
"Eunyoung and Mark have a beautiful home and have created the best “home away from home” for travelers. We thoroughly enjoyed our stay and look forward to returning next summer!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Property grounds
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
8.0 out of 10, Very good, (1)
"The property was perfect for our needs! My husband was able to work from the desk in the primary bedroom during the day while my mom and I shopped and explored nearby! Our dog LOVED the backyard and space to explore. We didn’t even need to go venture to the nearby dog park, but that was also super close! As out of towners, unfamiliar with locale, we would recommend bottled water for drinking. Everywhere we went was 5-15 min drive, we very much enjoyed our stay and grateful for the opportunity to...
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
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Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
A heated pool
Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
10.0 out of 10, Exceptional, (68)
"The house was great - just as listed and very comfortable / kid friendly. There wasn't a whole lot to do in the area over the holidays but we enjoyed the house, trampoline and jungle gym."
Summer in the Hamptons! Beautiful home with pool, hot tub, pirate ship and more!
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (25)
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
The Hampton Sack a cheerful relaxing beach cottage
Beach
The Hampton Sack a cheerful relaxing beach cottage
7.4 out of 10, Good, (12)
"Awesome break away from reality. Hope to return soon!"
The Hampton Sack a cheerful relaxing beach cottage
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
Pool
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, (5)
"We loved our stay here! The hosts were very helpful and communicative leading up to and during our short stay. The house was perfect for our family - the pool area is fantastic and being able to grill food at the outdoor kitchen is such a bonus. No back and forth to the house for snacks or drinks! We spent the evening around the fire pit and the extended deck meant that there was plenty of room for us to relax and our kids to play. We also explored the local area and nearby beaches. The property...
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
Property grounds
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
10.0 out of 10, Exceptional, (67)
"Lovely house, close to all with lots of room for a multi-generational family holiday! Would book again!"
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (73)
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Location and views! Located directly on Shinnecock Bay!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
Outdoor pool
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
10.0 out of 10, Exceptional, (1)
"Our overall expertise was great. Home was very clean and had all the essentials you need for a nice comfortable stay. The beds were very comfy, equipped with great linens and pillows. Home was cozy and comfortable. Can’t wait to stay again."
The price is £1,605
includes taxes & fees
3 Jun - 4 Jun
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
Unique Modern Barn House in Sag Harbor
Smart TV, fireplace
Unique Modern Barn House in Sag Harbor
10.0 out of 10, Exceptional, (10)
"Beautiful home with separate space for everyone and close to water and town!"
Unique Modern Barn House in Sag Harbor
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Property grounds
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, (9)
"my family and i grew up coming to hampton bays - and while myself and my parents have moved away - a family wedding brought us back to the area and we were so happy to stay local in this perfect home. it felt great to be back in the old neighborhood and not have to be cramped at my brothers home just a short 5 minute drive away. i hope we can stay again during our next trip!"
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Sabbatical a Private guest cottage in Sag Harbor
Exterior
Sabbatical a Private guest cottage in Sag Harbor
9.0 out of 10, Wonderful, (4)
"Beautiful studio apartment and truly a retreat from our busy work schedules. Nice response from host when we had questions. Lovely location and truly inspiring..."
Sabbatical a Private guest cottage in Sag Harbor
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, (7)
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Sun-loungers, beach towels
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (147)
"In town for a wedding - a large, convenient location that fulfilled the needs we had for that stay."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Cozy Sag Harbor Home Minutes from the Beach, Restaurants, Town Shopping
Interior
Cozy Sag Harbor Home Minutes from the Beach, Restaurants, Town Shopping
7.4 out of 10, Good, (3)
"We had a wonderful stay at the cottage. Very convenient to the town of Sag Harbor. House was very comfortable in every way. The only thing I would recommend is to outfit all of the windows with some kind of window coverings. Other than that, I would highly recommend a stay here."
Cozy Sag Harbor Home Minutes from the Beach, Restaurants, Town Shopping
Recently constructed modern-style home with a private pool, open-floor...
Smart TV, fireplace, ping pong, stereo
Recently constructed modern-style home with a private pool, open-floor...
Recently constructed modern-style home with a private pool, open-floor...
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See all available properties in Hamptons
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.

Hamptons Holiday Rental Travel Info

Popular accommodation
Hamptons private holiday homes
International airports
New York, NY (JFK-John F. Kennedy Intl.), Newark, NJ (EWR-Liberty Intl.) and New York, NY (LGA-LaGuardia)

Other types of properties in Hamptons you may be interested in

The Bentley Hotel Southampton
Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, (76)
"Large room recently updated, didn’t hear other guests "
The price is £198
includes taxes & fees
3 Jun - 4 Jun
The Bentley Hotel Southampton
The Atlantic Hotel
Outdoor pool
The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, (776)
"We enjoyed our stay and felt it was good value for the area. "
The price is £227
includes taxes & fees
3 Jun - 4 Jun
The Atlantic Hotel
Sag Harbor Inn
Outdoor pool
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (432)
"Nice B&B like "
The price is £264
includes taxes & fees
3 Jun - 4 Jun
Sag Harbor Inn
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.

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, apart-hotels, 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 £233 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. 

Recent reviews of Hamptons properties
Expedia verified reviews

Hamlet Inn

Hamlet Inn

5/5 Excellent
"Staff was very helpful and they made i have no problems with the late check-in. five star experience. Thanks - Ahmad"
A verified traveller stayed at Hamlet Inn
Posted 12 hours ago
Hamlet Inn