Southampton Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Southampton holiday rentals

Terrace/patio

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Southampton
9.8 out of 10, Exceptional, (21 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is HK$3,919
HK$6,653 total
includes taxes & fees
7 Jun - 8 Jun
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Outdoor dining

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.0 out of 10, Wonderful, (4 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
The price is HK$2,743
HK$4,602 total
includes taxes & fees
14 Jun - 15 Jun
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
The price is HK$4,938
HK$10,539 total
includes taxes & fees
4 Jun - 5 Jun
Minutes from the beach, brand new 3 bedroom
Outdoor pool, a heated pool

US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.

US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.
Southampton
10.0 out of 10, Exceptional, (23 reviews)
"Great property as advertised!!"
United States
robert b.
The price is HK$17,634
HK$29,092 total
includes taxes & fees
20 Jun - 21 Jun
US Open Championship Golf 2026. 6min, 2.6mi drive. In Southampton Village.
Exterior

Gorgeously Renovated SH Village 5 bd w/ Large Pool

Gorgeously Renovated SH Village 5 bd w/ Large Pool
Southampton
8.8 out of 10, Excellent, (6 reviews)
"Spacious and great location. Cleanliness and "
United States
Harry D.
The price is HK$31,348
HK$46,014 total
includes taxes & fees
17 Jun - 18 Jun
Gorgeously Renovated SH Village 5 bd w/ Large Pool
1 bedroom, bed sheets

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is HK$1,516
HK$2,323 total
includes taxes & fees
4 Jun - 5 Jun
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is HK$1,684
HK$2,650 total
includes taxes & fees
9 Jun - 10 Jun
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
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, (313 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 HK$1,866
HK$2,345 total
includes taxes & fees
7 Jun - 8 Jun
Windward Shores Ocean Resort
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (20 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,292
HK$2,619 total
includes taxes & fees
4 Jun - 5 Jun
North Fork Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (254 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$1,754
HK$2,345 total
includes taxes & fees
23 Jun - 24 Jun
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, (240 reviews)
"Very close to beach"
United States
Rabia
The price is HK$1,484
HK$1,951 total
includes taxes & fees
4 Jun - 5 Jun
Driftwood Resort
1 bedroom, bed sheets

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,684
HK$2,551 total
includes taxes & fees
8 Jun - 9 Jun
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,638
HK$2,498 total
includes taxes & fees
7 Jun - 8 Jun
American Beech in Greenport - Petite King Room 7
Fridge, microwave, oven, stovetop

Charming 1-bedroom apartment with AC in Sag Harbor

Charming 1-bedroom apartment with AC in Sag Harbor
Sag Harbor
The price is HK$2,081
HK$4,410 total
includes taxes & fees
9 Jun - 10 Jun
Charming 1-bedroom apartment with AC in Sag Harbor
Beach nearby

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$870
HK$3,859 total
includes taxes & fees
7 Jun - 8 Jun
Seabreeze 4 Charming Cottage walk to US Open
Smart TV, books

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is HK$4,498
HK$7,915 total
includes taxes & fees
7 Jun - 8 Jun
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is HK$2,998
HK$5,753 total
includes taxes & fees
4 Jun - 5 Jun
Northfork Townhouse walk to all
Dining

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is HK$2,531
HK$10,042 total
includes taxes & fees
7 Jun - 8 Jun
BlackBerry Private home with jacuzzi yearlong
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is HK$3,703
HK$7,759 total
includes taxes & fees
7 Jun - 8 Jun
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Beach nearby

Town walking distance-Bridgehampton Cottage

Town walking distance-Bridgehampton Cottage
Bridgehampton
9.4 out of 10, Exceptional, (10 reviews)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
United States
Jim M.
The price is HK$9,992
HK$14,577 total
includes taxes & fees
19 Jun - 20 Jun
Town walking distance-Bridgehampton Cottage
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
"Very clean"
Carol 1-night trip
Posted 2 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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  • 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 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.

What are some of the best holiday rentals that Southampton has to offer?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This highly rated holiday home rental in Southampton offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Southampton are Charming Two-Story Retreat in Southampton Village walk to town, beach and train. and Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️.

How many holiday rentals are there in Southampton?

Expedia has 554 holiday rentals for your stay in Southampton.

What can I see and do in Southampton?

Enjoy the outdoors at Cooper's Beach and Shinnecock East County Park, 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 Southampton Cultural Center.

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.