Hamptons Vacation Rentals

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Our top choices for Hamptons vacation rentals

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is CA $218
CA $286 total
includes taxes & fees
May 12 - May 13
Windward Shores Ocean Resort

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,341 reviews)
"Had a wonderful stay"
United States
Meghan
The price is CA $207
CA $263 total
includes taxes & fees
May 25 - May 26
Montauk Manor

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is CA $225
CA $272 total
includes taxes & fees
May 12 - May 13
Montauk Oceanside Suites

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is CA $213
CA $288 total
includes taxes & fees
May 19 - May 20
Driftwood Resort

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (281 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is CA $229
CA $336 total
includes taxes & fees
Jun 10 - Jun 11
The Surf Club

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is CA $720
CA $979 total
includes taxes & fees
May 12 - May 13
Offshore Residences

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $275
CA $374 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.8 out of 10, Excellent, (13 reviews)
"Great stay & great staff!"
United States
James
The price is CA $264
CA $302 total
includes taxes & fees
May 12 - May 13
North Fork Cottages & RV Resort

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Rocky Point
The price is CA $449
CA $842 total
includes taxes & fees
May 24 - May 25
Charming Rocky Point Home ~ 1 Mi to Beach!
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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Top Hamptons Hotel Reviews

Find out more about Hamptons

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.