Hamptons Holiday Rentals

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Holiday Rentals in Hamptons

View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (235)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$322
includes taxes & fees
19 May - 20 May
Windward Shores Ocean Resort
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
Property grounds
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
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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
Exterior
Sabbatical a Private guest cottage in Sag Harbor
10.0 out of 10, Exceptional, (3)
"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
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
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is NZ$1,585
includes taxes & fees
20 May - 21 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"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!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Microwave, oven, stovetop, coffee/tea maker
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
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
On the beach, sun-loungers, beach towels
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, (46)
"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.
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
A heated pool
Beautiful 4 to 5BR home with pool, hot tub & more in private beach community.
10.0 out of 10, Exceptional, (67)
"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."
Beautiful 4 to 5BR home with pool, hot tub & more in private beach community.
Beach
The Hampton Sack a cheerful relaxing beach cottage
7.2 out of 10, Good, (11)
"Truly no frills but key things work like heat and internet. Quite small but OK for 2 people."
The Hampton Sack a cheerful relaxing beach cottage
Fridge, microwave, oven, stovetop
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
9.8 out of 10, Exceptional, (16)
"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
Sun-loungers, beach towels
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (145)
"The house and area were excellent, just need some general maintenance as this property shows a lot of wear and tear. The restaurants, beach, area, and everything else were spectacular though."
The price is NZ$1,304
includes taxes & fees
29 May - 30 May
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
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
Exterior
Cozy Cottage by Shinnecock Canal and by Meschutt Beach! 🏖️
9.4 out of 10, Exceptional, (22)
"Our family of 4 stayed at this beautiful cottage while visiting family for the holidays. The home was clean and the beds were very comfortable. My husband and I have orthopedic issues so a comfortable bed is very important for us. I enjoyed the walks to the nearby canal. While it was winter, we would like to stay during the summer to enjoy their outside shower after a day at the beech and a bbq in their backyard. They are located only two minutes away from Meschutt beach. We’ve Enjoying this...
Cozy Cottage by Shinnecock Canal and by Meschutt Beach! 🏖️
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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

Outdoor pool
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (423)
"Kind and clean "
The price is NZ$436
includes taxes & fees
23 May - 24 May
Sag Harbor Inn
Outdoor pool
The Atlantic Hotel
2.5 star property
7.0 out of 10, Good, (767)
"Great prices, huge room, convenient and super friendly staff. Have stayed the past 3 weeks for business, good location"
The price is NZ$358
includes taxes & fees
28 May - 29 May
The Atlantic Hotel
Traditional Single Room, 1 King Bed
Southampton Inn
3.0 star property
8.4 out of 10, Very good, (478)
"The accommodations and the amenities were very nice."
The price is NZ$555
includes taxes & fees
29 May - 30 May
Southampton 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.

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