Town of Southampton Vacation Packages
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Top vacation destinations in Town of Southampton
Top Town of Southampton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Natirar
CA $2,437
per person
Nov 5 - Nov 8
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.8/10 Exceptional! (20 reviews)
One of the most beautiful hotels! The staff was incredibly accommodating. The rooms were beautiful and the amenities and spa were amazing. Highly recommend you find a reason to go!
Reviewed on Sep 29, 2026
Town of Southampton Hotel Deals
The Atlantic Hotel
1655 County Road 39 Southampton NY
CA $127
CA $181 total
Oct 30 - Oct 31
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Byłoby miło gdyby w pokoju oprócz kawy była także herbata."
Reviewed on Oct 1, 2026
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
CA $205
CA $234 total
Oct 13 - Oct 14
includes taxes & fees
9.6/10 Exceptional! (593 reviews)
"Kind of expected to be disappointed. However, really delighted. Room was lovely, clean and thoughtful appointments. Location was OK, but doable."
Reviewed on Oct 2, 2026
Faraway Sag Harbor
31 West Water Street Sag Harbor NY
CA $582
CA $732 total
Nov 2 - Nov 3
includes taxes & fees
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.
Frequently asked questions
How much does a Town of Southampton vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Town of Southampton from just CA $1,215. And the more you bundle, the more dollars you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Town of Southampton?
Bundling your hotel and flight with Expedia won't just save you time — it'll save you a few dollars too. A Town of Southampton vacation package makes it simple to create your ideal trip. With more than 550 airlines all over the world to choose from, finding flights that fit your schedule will be no sweat. In addition to that, we have over 1,000,000 hotels globally to take your pick of. Now that's choice! No matter who you are, Expedia puts more of the world within your reach.
Where should I stay in Town of Southampton?
A vacation in Town of Southampton isn't complete without seeing Coopers Beach, Wolffer Estates Vineyard and The Hamptons Beaches. Spend your nights near these attractions and make sightseeing a breeze.
What are the top hotels in Town of Southampton?
Travelers journeying to Town of Southampton often stay in Village of Southampton. Southampton Inn and The Atlantic Hotel are well-known options in this neighborhood. But it's not the only interesting place around town! Bay Point is also a great area and where you'll find Paddle Board Beach Sunsets Fine Dining Vineyards This Is The Ideal Getaway and Sag Harbor Beauty Walk To Beach Minutes From The Village.
How far in advance should I book my Town of Southampton vacation?
While not all airlines advertise tickets early, customers are usually able to compare international airfares on Expedia up to a year in advance. This is the time when you can score some fantastic deals. If you're purchasing tickets last minute, you might still be in luck. Sometimes the lowest prices become available a few weeks before departure.
What does an Expedia Town of Southampton travel package include?
Rental cars, hotels and flights, or any combination of them — you decide! Whether you're headed to Town of Southampton with the family or adventuring with your friends, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours and experiences?
What should I know before booking a Town of Southampton travel package?
An Expedia travel package can be customized for your budget and is a fantastic way to make your money go further. What you include is completely up to you. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with a Town of Southampton Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to choose from globally. With such a big range of choice, finding the perfect carrier to get you to Town of Southampton won't be difficult.
If I'm not able to travel, can I cancel my Town of Southampton vacation package?
It is possible to cancel your Town of Southampton booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
Stay near popular Town of Southampton attractions
Cooper's Beach
9.2/10 (171 reviews)
Escape NYC to play in the waves, sunbathe on fine, white sands or stroll past the exclusive mansions that line the dunes of one of the best beaches in the Hamptons.
Wolffer Estates Vineyard
9.4/10 (83 reviews)
Discover the country charm of the Hamptons by visiting this European-style winery with nearby equestrian center, outdoor wine bar and classy restaurants.
Ponquogue Beach
9.2/10 (70 reviews)
Stretching along a narrow strip of land on Long Island’s southern shoreline is this beautiful sandy beach. Relax in the sun or get active on the sand or water.
Parrish Art Museum
9.0/10 (9 reviews)
Browse the contemporary artwork displays, discover the talents of some the Hamptons best known artists and admire the barn-like design of this Long Island legend.
Photo by Sarah Sundberg
Westhampton Beach Performing Arts Center
8.6/10 (7 reviews)
Enjoy an outing to Westhampton Beach Performing Arts Center during your stay in Westhampton Beach. Wander the beautiful beaches in this quaint area.
Duck Walk Vineyards
Sample award-winning wines and take some bottles home as souvenirs when you visit one of two beautiful vineyards that have become Long Island institutions.
Shinnecock Hills Golf Course
8.6/10 (14 reviews)
Enjoy a round of golf in Tuckahoe at Shinnecock Hills Golf Course. While you're in the area, stroll along the beautiful beaches.
Meschutt Beach
8.6/10 (64 reviews)
If a restful vacation is part of your travel plans, Meschutt Beach might be the perfect place to seek out during your trip to Hampton Bays. While you're in the area, stroll along the seaside.
What to do in Town of Southampton
Full Day Private Long Island Wine Tours from New York City
CA $264
per adult
The Hamptons and Long Island Wineries Private Tour
CA $1,817
per traveller
Hamptons Private Day Trip from New York City
CA $1,817
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
