Holiday Homes in Hamptons

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Featured Holiday Homes in Hamptons

Beautiful Private 4 BR, Heated Pool. Close to Everything.

9.6 out of 10, Exceptional, (42)
"We were in the Hamptons to celebrate my sisters upcoming wedding and had a fantastic time in our rental the only complaint we had was that wish we were there longer!"
Beautiful Private 4 BR, Heated Pool. Close to Everything.

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

9.6 out of 10, Exceptional, (96)
"House was ideal for our extended family for thanksgiving weekend."
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

10.0 out of 10, Exceptional, (13)
"Steps to probably the most beautiful beach in the Hamptons. Thoroughly enjoyed our stay, as did the dogs. We will definitely be back."
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (168)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

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

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Beautiful Hamptons home close to beaches, shopping, & restaurants!

10.0 out of 10, Exceptional, (8)
"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "
Beautiful Hamptons home close to beaches, shopping, & restaurants!

Fall in thešŸŒ…beautiful sunsets

10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family memberā€™s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in thešŸŒ…beautiful sunsets

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

10.0 out of 10, Exceptional, (78)
"We loved our stay in this home! It was the perfect size for our extended family. It was well appointed. The kids loved playing in both levels of the garage. The kitchen had everything we needed. The beds were all comfy. We even took a dip in the cold pool! The owner was responsive to our requests and met all of our needs. I highly recommend this home!"
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

9.8 out of 10, Exceptional, (7)
"Family friendly, clean and well-stocked house with nice deck and pool for entertaining. It has personality. Well stocked kitchen (note - includes french press and a pod system but you need to bring your own pods; no coffee maker or kettle at time of our stay). Plenty of spices and condiments and entertaining ware as this is also their vacation home. Conveniently located near the highway and walkable to commercial area and 10 min drive to nearest beaches (it does back up to highway so gets road...
Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

Classic, Beautiful Farm House & Location!!!

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!"
Classic, Beautiful Farm House & Location!!!

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"We were a group age 3 to 75! The house was clean, well stocked and things for everyoneā€™s interest. Our host, Carrie, was kind and responsive. It will be a beautiful memory of spending time with our children and grandchildren. "
5 bedroom Private Family Get Away w/ Heated Pool

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

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

9.6 out of 10, Exceptional, (127)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Cozy Hamptons Beach House 1 Block from the Beach!

10.0 out of 10, Exceptional, (1)
"Great location between Montauk and East Hampton, easy to go between both. Great access to the beach."
Cozy Hamptons Beach House 1 Block from the Beach!

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Southampton estate with oversized pool, chefs kitchen, vast lawn,...

4.0 out of 10, (1)
"There was no hot water for half of our stay. Daniel from StayMarquis was helpful, but the emergency line did not call us back. Also a breaker needed to be reset the second night when we returned from an excursion. This impacted out stay for the price that we paid. I wrote a detailed email to the resolution department outlining these issues in hopes to be find a reasonable solution given the issues we faced, but unfortunately after 3 1/2 weeks, I have not received a response! The house is a...
Southampton estate with oversized pool, chefs kitchen, vast lawn,...

Hampton Bays Beach Oasis

9.6 out of 10, Exceptional, (10)
"We had a wonderful experience absolutely perfect for entertaining family and friends our first time renti g through VRBO. The accommodations were spectacular as well as comfortable. The owners were very accessible and we look forward to renting here again"
Hampton Bays Beach Oasis
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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Other property types in Hamptons

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AU$271
includes taxes & fees
18 Feb - 19 Feb
Windward Shores Ocean Resort

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball
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.