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

Southampton Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Southampton vacation rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (29 reviews)
"Great stay & great staff!"
United States
James
The price is NT$11,954
NT$13,657 total
includes taxes & fees
Jul 21 - Jul 22
North Fork Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (266 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is NT$13,114
NT$16,375 total
includes taxes & fees
Jul 13 - Jul 14
Cliffside Resort Condominiums
Individually decorated, individually furnished, iron/ironing board

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 NT$19,774
NT$23,466 total
includes taxes & fees
Jul 23 - Jul 24
Windward Shores Ocean 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

Harpoon House

Harpoon House

8/10 Good
"Room was good. We're seniors and the 2 flights of stairs to the room were a chore for us. Staff did carry the suitcase to the room."
EDWARD 1-night trip
Posted 3 days ago
Harpoon House

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Southampton
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Look no further and take a look at our great range of rental properties in Southampton!

Frequently asked questions

Can I find vacation rentals in Southampton?

Yes, you can find vacation rentals in Southampton close to Southampton Cultural 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 vacation rentals are there in Southampton?

Expedia has 502 vacation 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 Southampton Cultural Center and Shinnecock Hills Golf Course.

What are vacation rentals like in Southampton?

Vacation rentals are private properties you can reserve for a short or long stay in Southampton. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.