Book Holiday Homes in Southampton

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Featured Holiday Homes in Southampton

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Southampton
When you stay at this vacation home in Southampton, you'll be by the sea, a 4-minute drive from The Hamptons Beaches and 6 minutes from Cooper's Beach.
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Charming Village home in the heart of Southampton

Charming Village home in the heart of Southampton

Southampton
When you stay at this vacation home in Southampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.
Charming Village home in the heart of Southampton
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
Located in Southampton, this vacation home is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
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Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

Southampton
With a stay at this vacation home in Southampton, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Elizabeth A. Morton National Wildlife ...
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families

Southampton
With a stay at this vacation home in Southampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Elizabeth A. Morton National ...
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
Mary's Gated Oasis Private Estate

Mary's Gated Oasis Private Estate

Southampton
With a stay at this vacation home in Southampton, you'll be within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Mary's Gated Oasis Private Estate
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...

Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...

Southampton
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

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

Southampton
The price is AU$8,978 per night from 24 May to 25 May
AU$8,978
includes taxes & fees
24 May - 25 May
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Southampton
With a stay at this vacation home in Southampton, you'll be by the sea, just a 5-minute walk from The Hamptons Beaches and within a 5-minute drive of Elizabeth ...
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.
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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.

Southampton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Southampton vacation homes are the perfect way for you to wing it.

Holiday houses in Southampton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Southampton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Southampton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southampton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Southampton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Southampton Holiday Homes essential information

Accommodation
276 Holiday Homes
Lowest Price
AU$236
Highest Price
AU$8,978
Popular accommodation
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 , Charming Village home in the heart of Southampton, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa, Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families, Mary's Gated Oasis Private Estate, Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,..., Contemporary Southampton Village Home Walking Distance to Town, Pool,..., Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Top trending hotels in Southampton

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is AU$265 per night from 28 Apr to 29 Apr
AU$265
includes taxes & fees
28 Apr - 29 Apr
When you stay at The Atlantic Hotel in Southampton, you'll be in the business district, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
Fully refundableReserve now, pay when you stay
The price is AU$296 per night from 28 Apr to 29 Apr
AU$296
includes taxes & fees
28 Apr - 29 Apr
When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt ...
The Bentley Hotel Southampton
Southampton Inn

Southampton Inn

3 out of 5
91 Hill Street, Southampton, NY
The price is AU$412 per night from 25 Apr to 26 Apr
AU$412
includes taxes & fees
25 Apr - 26 Apr
Located in Southampton, Southampton Inn is in a shopping district, a 5-minute walk from Southampton Cultural Center and 6 minutes by foot from Southampton Arts ...
Southampton Inn
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Hamlet Inn

Hamlet Inn

2 out of 5
300 Montauk Highway, Southampton, NY
The price is AU$236 per night from 27 Apr to 28 Apr
AU$236
includes taxes & fees
27 Apr - 28 Apr
When you stay at Hamlet Inn in Southampton, you'll be by the ocean, within a 5-minute drive of Shinnecock Hills Golf Course and Southampton Cultural Center.
Hamlet Inn
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.