Southampton Holiday Rentals

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Holiday Rentals in Southampton

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
2.0 star property
9.0 out of 10, Wonderful, (4)
"The location is great, the home is spacious, and the host is very responsive. However, the house itself could really use some sprucing up. I’d recommend replacing all the bed linens and fixing the broken lamps. "
United States
Juliana H.
The price is HK$2,720
HK$4,536 total
includes taxes & fees
3 Nov - 4 Nov
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Minutes from the beach, brand new 4 bedroom
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is HK$3,497
HK$8,620 total
includes taxes & fees
4 Nov - 5 Nov
Minutes from the beach, brand new 4 bedroom
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
9.0 out of 10, Wonderful, (10)
"We had a very relaxing stay at Irene's English Cottage in Southampton. The house had all of the amenities, comfortable beds, beach towels, a big kitchen with a large dining room table, air conditioning, a beautiful pool in the backyard. We were able to walk home after having dinner in town back to the house. Irene has also beautifully designed the interior of the home. Thank you, Irene!"
United States
Richard A. F.
The price is HK$8,434
HK$13,950 total
includes taxes & fees
1 Dec - 2 Dec
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
North Fork Cottages & RV Resort
3.0 star property
The price is HK$1,515
HK$1,731 total
includes taxes & fees
3 Nov - 4 Nov
North Fork Cottages & RV Resort
Hidden gem! Southampton beach cottage
10.0 out of 10, Exceptional, (1)
The price is HK$427
HK$3,533 total
includes taxes & fees
9 Nov - 10 Nov
Hidden gem! Southampton beach cottage
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (16)
"A new clean cozy space. Perfect for a weekend getaway. Very easy experience. Highly recommended!"
United States
John W.
The price is HK$1,203
HK$2,937 total
includes taxes & fees
4 Nov - 5 Nov
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Cozy quiet gem, private & fenced in backyard
9.4 out of 10, Exceptional, (3)
"Just hubby & I. Great fireplace and deck with very clean bubbly hot tub. Comfy king-sized bed. Kitchen was clean & functional with basics. Backyard appeared larger in pictures. Rental could use extra couch in living room to comfortably fit eight ppl. The living room couch is just for sitting, appears larger in pictures. Couch is"
United States
STEPHANIE C.
The price is HK$583
HK$6,845 total
includes taxes & fees
6 Nov - 7 Nov
Cozy quiet gem, private & fenced in backyard
Private beach on a fenced in property sunset views
10.0 out of 10, Exceptional, (12)
"Beautiful sunrise, sunsets and scenery. Beautiful property"
United States
Elaine P.
The price is HK$1,546
HK$10,387 total
includes taxes & fees
3 Nov - 4 Nov
Private beach on a fenced in property sunset views
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (244)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is HK$1,740
HK$2,325 total
includes taxes & fees
3 Nov - 4 Nov
Cliffside Resort Condominiums
Year-Round Private Jacuzzi / Peaceful Fenced Yard
9.6 out of 10, Exceptional, (22)
"What a great place for a family gathering! The backyard is to die for and the host was very helpful throughout the stay. We’ll be back!!"
United States
Lisa w.
The price is HK$769
HK$9,881 total
includes taxes & fees
9 Nov - 10 Nov
Year-Round Private Jacuzzi / Peaceful Fenced Yard
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
10.0 out of 10, Exceptional, (6)
"Our family / extended family was in town for over a week for the Hampton Classic horse show. We all enjoyed or stay at this wonderful home: beautiful newly renovated open space, outstanding kitchens (indoors and outdoors), numerous areas to have separate down time, excellent in suite bedroom / bathrooms including three bedrooms suites with king beds, fabulous backyard with a private pool, and exceptionally clean with all amenities needed. The owners were also incredible; extremely responsive,...
United States
Kristin C.
The price is HK$20,980
HK$42,585 total
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
Stylish Woody Interior 1BR+Loft w/ Beach Access
The price is HK$4,274
HK$7,793 total
includes taxes & fees
4 Nov - 5 Nov
Stylish Woody Interior 1BR+Loft w/ Beach Access
Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$15,502
HK$18,773 total
includes taxes & fees
23 Nov - 24 Nov
Canoe Place Waterfront Residences
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
10.0 out of 10, Exceptional, (104)
"2 friends and I rented John's place for a mini reunion. It was perfect for us. Very clean, very cutely decorated, loved the access to the bay, and sitting on the swings overlooking the bay. Geat deck to eat and relax. Though we didn't meet our host, he answered all of our communications in a timely fashion."
United States
Ruth E.
The price is HK$3,302
HK$6,090 total
includes taxes & fees
1 Dec - 2 Dec
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is HK$1,943
HK$4,314 total
includes taxes & fees
5 Nov - 6 Nov
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,391
HK$2,175 total
includes taxes & fees
10 Nov - 11 Nov
American Beech in Greenport - Petite King Room 7
Spacious 5-bedroom house with water views and 2 houses from the bay.
The price is HK$31,081
HK$50,087 total
includes taxes & fees
7 Nov - 8 Nov
Spacious 5-bedroom house with water views and 2 houses from the bay.
Orient Village — Historic Bayfront Cottage — 2025 Season
10.0 out of 10, Exceptional, (23)
"Step away from your busy schedule, step back in time, and step down to the beach. Bayside Cottage is an idyllic, charming, and rare place -- one increasingly harder to find as grandiose properties populate many parts of the Island. Thankfully the North Fork has retained much of its character since we began visiting some 20 years ago, and Orient is beautifully preserved with a lot of tender loving care, especially towards nature. It was turtle season in June! At Bayside, circa 1887, one doesn't...
United States
Jennifer G.
The price is HK$2,331
HK$5,513 total
includes taxes & fees
30 Nov - 1 Dec
Orient Village — Historic Bayfront Cottage — 2025 Season
Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is HK$4,662
HK$9,126 total
includes taxes & fees
3 Nov - 4 Nov
Beautifully farmhouse
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

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 holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, 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?

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...: This highly rated holiday home rental in Southampton offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a stovetop, a microwave and a coffee maker, so that you can cook with friends or family. Some other top choices in Southampton are Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping and Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families.

How many holiday rentals are there in Southampton?

Expedia has 482 holiday 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 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.