A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

Southampton Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southampton holiday rentals

1. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (322 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is S$338
includes taxes & fees
27 Sept - 28 Sept
Windward Shores Ocean Resort

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (289 reviews)
"Great place!"
United States
Christine
The price is S$552
includes taxes & fees
21 Sept - 22 Sept
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (51 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is S$430
includes taxes & fees
13 Sept - 14 Sept
North Fork Resort

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (248 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is S$285
includes taxes & fees
21 Sept - 22 Sept
Driftwood Resort
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 Southampton Hotel Reviews

Southampton Inn

Southampton Inn

10/10 Excellent
"Kind of a mean front office, but great property."
Christopher 1-night trip
Posted 6 days ago
Southampton Inn
Sea Haven Resort Motel

Sea Haven Resort Motel

10/10 Excellent
"Friendly staff and pleasant stay, pet friendly and perfect location. Bill and Omar were helpful and great!!"
Bonnie 1-night trip
Posted 4 months ago
Sea Haven Resort Motel

Frequently asked questions

Can I find holiday rentals in Southampton?

Yes, there are holiday rentals in Southampton close to Southampton Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Southampton. Make sure you have time to check out the museums and festivals during your trip.

How many holiday rentals are there in Southampton?

Expedia has 494 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and The Hamptons Beaches, or simply take in cultural attractions like Shinnecock Nation Cultural Center and Museum and Southampton Historical Museum. Other places in town to visit include Southampton Arts Center and Shinnecock Hills Golf Course.

What are holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.