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
Stay at this vacation home in Southampton. Enjoy free WiFi, a garden, and patios. Popular attractions The Hamptons Beaches and Our Lady of Poland Catholic Church ...
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Sprawling Southampton Home: Private Pool

Sprawling Southampton Home: Private Pool

Southampton
Stay at this vacation home in Southampton. Enjoy private pools, patios, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular ...
Sprawling Southampton Home: Private Pool
Charming Village home in the heart of Southampton

Charming Village home in the heart of Southampton

Southampton
Stay at this vacation home in Southampton. Enjoy free WiFi, private pools, and patios. Popular attractions The Hamptons Beaches and North Main Street Historic ...
Charming Village home in the heart of Southampton
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Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton
Book a stay at this family-friendly vacation home in Southampton. Enjoy free WiFi, private pools, and a garden. Popular attractions Southampton Golf Range and ...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
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
Stay at this vacation home in Southampton. Enjoy private pools, a fitness center, and tennis courts. Popular attractions The Hamptons Beaches and Noyac Golf ...
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
Stay at this vacation home in Southampton. Enjoy private pools, patios, and an in-room coffeemaker. Popular attractions The Hamptons Beaches and North Sea Bathing ...
Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families
Mary's Gated Oasis Private Estate

Mary's Gated Oasis Private Estate

Southampton
Stay at this vacation home in Southampton. Enjoy a pool table, in-room fireplaces, and air conditioning. Popular attractions The Hamptons Beaches and North Sea ...
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
Stay at this vacation home in Southampton. Enjoy private pools, a fitness center, and patios. Popular attractions Shinnecock Hills Golf Course and Shinnecock ...
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
Stay at this vacation home in Southampton. Enjoy private pools, patios, and cable/satellite TV service. Popular attractions The Hamptons Beaches and National ...
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
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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
NZ$337
Highest Price
NZ$600
Popular accommodation
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 , Sprawling Southampton Home: Private Pool, 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,...

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 NZ$337 per night from 6 Apr to 7 Apr
NZ$337
includes taxes & fees
6 Apr - 7 Apr
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
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 NZ$357 per night from 14 Apr to 15 Apr
NZ$357
includes taxes & fees
14 Apr - 15 Apr
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Bentley Hotel Southampton
Southampton Inn

Southampton Inn

3 out of 5
91 Hill Street, Southampton, NY
The price is NZ$452 per night from 6 Apr to 7 Apr
NZ$452
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star family-friendly hotel in Southampton. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Popular attractions The Hamptons Beaches and ...
Southampton Inn
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The 1708 House

The 1708 House

3 out of 5
126 Main St, Southampton, NY
The price is NZ$600 per night from 26 Apr to 27 Apr
NZ$600
includes taxes & fees
26 Apr - 27 Apr
Stay at this 3-star B&B in Southampton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Hamptons Beaches and Southampton Historical ...
The 1708 House
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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.