Hamptons Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Hamptons

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 237 reviews
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$451
per night
2 Jun - 3 Jun
Windward Shores Ocean Resort
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
8.0 out of 10, Very good, 1 review
"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!
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, 47 reviews
"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
Save an average of 15% on thousands of hotels when you're signed in
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 48 reviews
"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
10.0 out of 10, Exceptional, 11 reviews
"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
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 73 reviews
"We had the best time at Rick’s house in the Hamptons! We’d love to come back!"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Sabbatical a Private guest cottage in Sag Harbor
10.0 out of 10, Exceptional, 3 reviews
"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
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, 147 reviews
"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
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, 46 reviews
"Traveling with family and dog... private walk to the beach, stylish but simple, comfortable beds, clean and organized, responsive management... 2 bedrooms downstairs, one entire 2nd floor master bedroom / entertaining space upstairs, and an attached 'cottage' king studio that is attached to the main house."
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Only a few weeks still available. Relax in the Hamptons. Pool, hot tub and more!
10.0 out of 10, Exceptional, 67 reviews
"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."
Only a few weeks still available. Relax in the Hamptons. Pool, hot tub and more!
The Hampton Sack a cheerful relaxing beach cottage
7.4 out of 10, Good, 12 reviews
"Awesome break away from reality. Hope to return soon!"
The Hampton Sack a cheerful relaxing beach cottage
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, 9 reviews
"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
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road
10.0 out of 10, Exceptional, 67 reviews
"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
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, 12 reviews
"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!
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, 7 reviews
"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
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, 22 reviews
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
10.0 out of 10, Exceptional, 1 review
"The house was perfect and clean. We really enjoyed the screened in patio."
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, 5 reviews
"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
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
9.8 out of 10, Exceptional, 16 reviews
"This property was just what my family and I were looking for. A quaint and quiet house with a small town feel. We stayed for NYE hoping to get away from the loud chaos we’re typically faced with at home and this location fit the bill. Pros: I’m not sure how this changes in the summer months but things were mostly quiet. There are restaurants, coffee, and food shopping all within a 5 minute drive. The home itself is pretty small, so for the 4 of us- husband, 17y/o, 9 y/o, and myself, it was...
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
Don't see what you're looking for?
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.

Other types of properties in Hamptons you may be interested in

The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, 76 reviews
"Large room recently updated, didn’t hear other guests "
The price is NZ$343
per night
3 Jun - 4 Jun
The Bentley Hotel Southampton
The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, 774 reviews
"We enjoyed our stay and felt it was good value for the area. "
The price is NZ$368
per night
2 Jun - 3 Jun
The Atlantic Hotel
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, 431 reviews
"Nice B&B like "
The price is NZ$551
per night
2 Jun - 3 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hamptons holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hamptons. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Hamptons. Seeing all the best attractions is bound to make you fall in love with Hamptons. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Hamptons short-term rentals, that won’t be hard to do.

Recent reviews of Hamptons properties
Expedia verified reviews