Town of Southampton Vacation Packages

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Top vacation destinations in Town of Southampton

A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

Southampton

Southampton
A sandy beach path with wooden fences on either side leading to the ocean.

Hampton Bays

Hampton Bays
A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Sag Harbor

Sag Harbor

Top Town of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane

Seven Beach Lane

CA $1,535
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (32 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.

Reviewed on Aug 21, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
CA $2,692
per person
Oct 16 - Oct 24
just found
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,902 reviews)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

North End
CA $2,411
per person
Oct 14 - Oct 18
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
No reviews
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $2,054
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Great stay

Reviewed on Aug 23, 2026

Hilton Garden Inn New York/Manhattan-Chelsea

Hilton Garden Inn New York/Manhattan-Chelsea

Manhattan
CA $2,512
per person
Oct 16 - Oct 24
just found
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8/10 Very good! (3,164 reviews)

Town of Southampton Hotel Deals

The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $271
CA $344 total
Sep 8 - Sep 9
includes taxes & fees
7.2/10 Good! (1,008 reviews)
"Well it needs updating and renovating. The busy road is loud and it’s so difficult turning left or right out of the parking lot because this is the WORST traffic area in SH."

Reviewed on Aug 23, 2026

The Atlantic Hotel
 Hampton's Vacation Inn

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY
CA $279
CA $318 total
Aug 31 - Sep 1
includes taxes & fees
Hampton's Vacation Inn
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
Fully refundableReserve now, pay when you stay
CA $167
CA $191 total
Aug 26 - Aug 27
includes taxes & fees
6.8/10 (864 reviews)
"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front ..."

Reviewed on Aug 21, 2026

Budget Host East End
See all 1,951 properties in Town of Southampton
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 $1,535. 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

A beach with sand dunes and a person walking along the shore.

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.
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A wooden barrel with the text "CADUS - France - Sensoriel 2013 ACCESS 22mm-French oak-30 months air dried ML+Pur Process WOLFFER ESTATE VINEYARD".

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.
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A sandy beach path with wooden fences on either side leading to the ocean.

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.
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An art gallery with a wooden ceiling and a long hallway displaying various artworks.

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.
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A sign for the Shinnecock Nation Cultural Center and Museum with a wooden building in the background.

Shinnecock Nation Cultural Center and Museum

9.6/10 (5 reviews)
Learn about the traditional ways of life of the Shinnecock and admire indigenous artworks in Long Island’s only Native American-owned and operated museum.
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A two-story brick building with a marquee sign reading "WESTHAMPTON" and an American flag above the entrance.
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.
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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.
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What to do in Town of Southampton

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

CA $209
per adult
Sunday Brunch Sail in Greenport
great fun with friends

Full Day Private Long Island Wine Tours from New York City

CA $265
per adult
Full Day Private Long Island Wine Tours from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,824
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Town of Southampton
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.