Southampton Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

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
10.0 out of 10, Exceptional, (17 reviews)
"Great host & location. Would stay again"
United States
Chris H.
The price is HK$3,917
HK$6,649 total
includes taxes & fees
1 Jun - 2 Jun
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is HK$3,525
HK$8,690 total
includes taxes & fees
8 May - 9 May
Minutes from the beach, brand new 4 bedroom
Property grounds

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is HK$14,080
HK$19,724 total
includes taxes & fees
6 May - 7 May
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Living area

Minutes from the beach, brand new 3 bedroom

Minutes from the beach, brand new 3 bedroom
Southampton
The price is HK$5,287
HK$10,990 total
includes taxes & fees
16 May - 17 May
Minutes from the beach, brand new 3 bedroom
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$1,683
HK$2,550 total
includes taxes & fees
25 May - 26 May
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$1,683
HK$2,648 total
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
1 bedroom, bed sheets

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Safari Tent Glamping,S6-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
United States
Lorraine
The price is HK$1,683
HK$2,550 total
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
Flat-screen TV

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is HK$1,441
HK$1,646 total
includes taxes & fees
13 May - 14 May
North Fork Cottages & RV Resort
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, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is HK$1,247
HK$1,638 total
includes taxes & fees
6 May - 7 May
Windward Shores Ocean Resort
Exterior

Seabreeze #4 Charming Cottage just 2.5 miles to US Open

Seabreeze #4 Charming Cottage just 2.5 miles 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$619
HK$3,539 total
includes taxes & fees
6 May - 7 May
Seabreeze #4 Charming Cottage just 2.5 miles to US Open
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is HK$1,578
HK$2,143 total
includes taxes & fees
31 May - 1 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, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is HK$1,220
HK$1,649 total
includes taxes & fees
19 May - 20 May
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$1,683
HK$2,550 total
includes taxes & fees
21 May - 22 May
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
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is HK$1,559
HK$2,381 total
includes taxes & fees
6 May - 7 May
American Beech in Greenport - Petite King Room 7
1 bedroom, free WiFi, bed sheets

Hamptons apartment getaway

Hamptons apartment getaway
East Quogue
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is HK$1,175
HK$2,291 total
includes taxes & fees
6 May - 7 May
Hamptons apartment getaway
Dining

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (1 review)
"The host was very welcoming and the house was very clean"
United States
James W.
The price is HK$1,488
HK$2,971 total
includes taxes & fees
1 Jun - 2 Jun
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Exterior detail

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$3,518
HK$6,641 total
includes taxes & fees
8 May - 9 May
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
TV, fireplace, stereo, offices

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
The price is HK$6,768
HK$12,958 total
includes taxes & fees
20 May - 21 May
East Hampton Estate for 10, Pool Open! Sauna, Chef`s Kitchen, Outdoor Fireplace
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$2,467
HK$5,012 total
includes taxes & fees
6 May - 7 May
Northfork Townhouse walk to all
Smart TV, fireplace, video games, stereo

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Center Moriches
10.0 out of 10, Exceptional, (116 reviews)
"Quick and kind communication, beautiful location and the most comfortable beds! An absolute must-stay for anyone coming to the area."
United States
Stephanie M.
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
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 Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Nice place to stay."
Robert 3-night trip
Posted 14 hours ago
The Atlantic Hotel

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
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • 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 551 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.