Holiday Homes in Hamptons

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Featured Holiday Homes in Hamptons and around

Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool

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
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Outdoor pool, a heated pool

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Exquisite New Hampton Home in a Perfect Location
Interior

Exquisite New Hampton Home in a Perfect Location

Exquisite New Hampton Home in a Perfect Location
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Property grounds

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
5 bedroom Private Family Get Away w/ Heated Pool
Outdoor pool, a heated pool

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 everyone’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
Fall in the🌅beautiful sunsets

Fall in the🌅beautiful sunsets

10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family member’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 the🌅beautiful sunsets
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (17)
"Had the best girls weekend with old college roommates! The house is stunning and incredibly clean. Was well stocked with everything we needed for our stay. Great location as well for checking out downtown, the beach, wineries, etc. "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
A Quiet Place in the Hamptons
Outdoor pool, a heated pool

A Quiet Place in the Hamptons

9.8 out of 10, Exceptional, (34)
"We had a very nice time. The house was exactly what we needed and was close to everything. "
A Quiet Place in the Hamptons
Beautiful Private 4 BR, Heated Pool. Close to Everything.
Outdoor pool, a heated pool

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.
Exclusive location with spacious interior offering many amenities.
Interior

Exclusive location with spacious interior offering many amenities.

7.8 out of 10, Good, (7)
"Everything was exactly as advertised! We appreciated the space as it made our weekend extra special, location was especially convenient. Overall a great experience! Thank you."
Exclusive location with spacious interior offering many amenities.
Secluded Southampton Home That Has It All
Pool

Secluded Southampton Home That Has It All

10.0 out of 10, Exceptional, (1)
"This was a perfect getaway for a multigenerational family reunion! It's a beautifully maintained property. The bathroom to bedroom ratio was great for many families/couples. Great amenities included a heated pool and jacuzzi, and it's ideally located with easy access to Southampton and Sag Harbor downtown areas. Bob was a wonderful host and easy to reach. I recommend this place for anyone planning a family getaway. "
Secluded Southampton Home That Has It All
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Outdoor pool, a heated pool

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo

Mid-Century Fall 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 Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (167)
"Group of 6 women getting together. Beautiful spacious home. We all had our own bedrooms. Having 4.5 baths was great. Plenty of space for all of us. Host was excellent and had great recommendations. Quick ride to the beautiful beach. "
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Summer getaway
Outdoor pool, a heated pool

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Terrace/patio

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
Unique Modern Barn House in Sag Harbor
Smart TV, fireplace

Unique Modern Barn House in Sag Harbor

10.0 out of 10, Exceptional, (16)
"I was looking for a quiet luxury home between Boston and New York where our children could meet up with their parents and spend Thanksgiving week. Never been to Long Island/Sag Harbor so I was looking forward to seeing the area. This is a beautiful home with everything, literally. Kitchen and supplied cooking tools and appliances were beyond awesome. A Miele in wall coffee maker. Wed are all foodies so did pretty much all of our own cooking. 3 ovens, one of which is a steam oven. Silverware,...
Unique Modern Barn House in Sag Harbor
Brand New in the Heart of East Hampton Village with Pool
Outdoor dining

Brand New in the Heart of East Hampton Village with Pool

10.0 out of 10, Exceptional, (26)
"Spacious, like new in the heart of downtown East Hampton. Great house for families. Owner was accommodating and we will return. "
Brand New in the Heart of East Hampton Village with Pool
Welcome to the J Luxury Southampton Estate w/Pool
Pool

Welcome to the J Luxury Southampton Estate w/Pool

9.8 out of 10, Exceptional, (30)
"Joe was an amazing host - always responsive from the moment of booking throughout the entire stay. The kitchen was a chef's dream - spacious and stocked with every appliance, seasoning, etc you can think of. We were a group of 8 and cooked family dinners each night. The highlight of the property was most definitely the deck, which was beautifully decorated and with a perfect amount of seating. Neighborhood was very walkable and it was a very short drive to the beach! I would note that there are...
Welcome to the J Luxury Southampton Estate w/Pool
Sag Harbor Village Gem
Property grounds

Sag Harbor Village Gem

10.0 out of 10, Exceptional, (40)
"House is beautiful, big, and very clean. Property Owwner communicated with us making sure evrything was great. "
Sag Harbor Village Gem
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
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is €159
includes taxes & fees
5 Jan - 6 Jan 2025
Windward Shores Ocean Resort
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool

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
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Outdoor pool, a heated pool

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
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.