Town of Southampton Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
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Southampton

Southampton

Top Town of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Price was CA $1,701, price is now CA $1,124 per person
CA $1,124
per person
Dec 31 - Jan 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,054 reviews)
It’s October in nyc: 70*+ every day. The hotel decided to put the heater on and disable a/c except for the suites on the 16th floor. I cancelled my room after it wouldn’t get below 75* after hours of the window open (only opens like an inch). Staff were accommodating with the cancellation but basically just tried rationalizing the crazy room temps / lack of A/C. Most hotels in the city do this in winter .. not when it’s still hot out.

Reviewed on Oct 30, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,023, price is now CA $2,374 per person
CA $2,374
per person
Jan 12 - Jan 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

The Mark

The Mark

5 out of 5
Manhattan
Price was CA $7,966, price is now CA $4,902 per person
CA $4,902
per person
Jan 12 - Jan 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.6/10 Exceptional! (723 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,262, price is now CA $2,748 per person
CA $2,748
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $5,261, price is now CA $3,450 per person
CA $3,450
per person
Jan 12 - Jan 19
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.6/10 Exceptional! (286 reviews)

Town of Southampton Hotel Deals

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $145 per night from Nov 24 to Nov 25
CA $145
CA $200 total
Nov 24 - Nov 25
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"I traveled several hours and arrived early the young lady at the front desk was extremely helpful and got me in a room immediately. I was able to shower and dress before my event. Hotel was clean and very comfortable I slept well. I will definitely stay here again."

Reviewed on Oct 31, 2026

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 CA $225 per night from Nov 2 to Nov 3
CA $225
CA $257 total
Nov 2 - Nov 3
includes taxes & fees
The Bentley Hotel Southampton
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2 out of 5
2 W Montauk Hwy Hampton Bays NY
The price is CA $178 per night from Nov 6 to Nov 7
CA $178
CA $203 total
Nov 6 - Nov 7
includes taxes & fees
Hampton Bays Hotel on Main
See all 1,935 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Family Vacations

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 $1,124. 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.
See properties

What to do in Town of Southampton

great fun with friends

Full Day Private Long Island Wine Tours from New York City

CA $267
per adult
Full Day Private Long Island Wine Tours from New York City
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.