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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Southampton vacation rentals

Iron/ironing board, WiFi (free), individually decorated

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 NT$7,171
NT$9,059 total
includes taxes & fees
Sep 21 - Sep 22
Windward Shores Ocean Resort
Condo | Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
The price is NT$9,789
NT$14,031 total
includes taxes & fees
Sep 7 - Sep 8
Cliffside Resort Condominiums
Flat-screen TV

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NT$10,236
NT$11,695 total
includes taxes & fees
Sep 10 - Sep 11
North Fork Resort
Apartment | WiFi (free), individually decorated, individually furnished, bed sheets

4. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (247 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is NT$5,319
NT$7,115 total
includes taxes & fees
Sep 21 - Sep 22
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

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

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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  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

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 494 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 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 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.