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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Southampton vacation rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ₩224,050
₩403,043 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
Room

2. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (331 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is ₩177,453
₩238,712 total
includes taxes & fees
Oct 29 - Oct 30
Windward Shores Ocean Resort
Property grounds

3. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is ₩153,913
₩219,038 total
includes taxes & fees
Oct 30 - Oct 31
Driftwood Resort
A modern house with a deck, outdoor seating, and a fire pit.

4. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (70 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ₩425,109
₩485,688 total
includes taxes & fees
Oct 29 - Oct 30
North Fork 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

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Excellent facility all as advertised The folks there are great"
Aaron 4-night trip
Posted 23 hours ago
The Bentley Hotel Southampton

Find out more about Southampton

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

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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 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 vacation rentals are there in Southampton?

Expedia has 481 vacation 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 Southampton Historical Museum and Halsey House. Other places in town to visit include Southampton Arts 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.