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
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Southampton holiday rentals

Iron/ironing board, free WiFi, individually decorated

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (319 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 S$711
includes taxes & fees
19 Jul - 20 Jul
Windward Shores Ocean Resort
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (30 reviews)
"Great stay & great staff!"
United States
James
The price is S$549
includes taxes & fees
22 Jul - 23 Jul
North Fork Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (271 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is S$666
includes taxes & fees
22 Jul - 23 Jul
Cliffside Resort Condominiums
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (242 reviews)
"Very close to beach"
United States
Rabia
The price is S$619
includes taxes & fees
9 Aug - 10 Aug
Driftwood Resort
Interior

Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
The price is S$2,211
includes taxes & fees
5 Aug - 6 Aug
Hamptons Vacation Rental w/ Saltwater Pool
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 Long Island Hotel

Southampton Long Island Hotel

10/10 Excellent
"We had a great stay overall. Everything was very clean, and the staff was incredibly friendly and welcoming. The room was comfortable, and we really appreciated the excellent service. The only constructive feedback I’d like to share is about the toiletries. The soap and shampoo provided were very low quality and came in very small amounts. Unfortunately, they caused some skin irritation for me. Considering the price of the hotel, I think it would be worth investing in better-quality toiletries. There are many affordable options that would greatly improve the guest experience."
Mariakamila 1-night trip
Posted 16 hours ago
Southampton Long Island Hotel

Frequently asked questions

Can I find holiday rentals in Southampton?

Yes, there are holiday rentals in Southampton close to Shinnecock Nation Cultural Center and Museum, 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 503 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at The Hamptons Beaches and Cooper's Beach, or simply take in cultural attractions like Shinnecock Nation Cultural Center and Museum and Southampton Historical Museum. Other places in town to visit include North Main Street Historic District 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.