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*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top vacation destinations in Town of Southampton

FlightsFlightsHotelsHotels

Southampton

Southampton

Top Town of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,595, price is now CA $964 per person
CA $964
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (4,409 reviews)
The trip was amazing .. everything went so smoothly

Reviewed on May 25, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $5,697, price is now CA $2,876 per person
CA $2,876
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $2,180, price is now CA $1,410 per person
CA $1,410
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,520 reviews)
Staff was helpful and friendly.

Reviewed on May 23, 2026

Sound View Greenport

Sound View Greenport

4 out of 5
Price was CA $3,622, price is now CA $2,391 per person
CA $2,391
per person
Aug 11 - Aug 16
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (646 reviews)
Clean rooms, great continental breakfast. Was upgraded to waterfront room!!

Reviewed on May 3, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,841, price is now CA $3,212 per person
CA $3,212
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Bare concrete floors in bathroom, freaking cold and it’s summer outside. How cold does that floor get at winter… Shower door needs a seal at the bottom so water doesn’t flow out in front of sink. Huge puddles flow out.

Reviewed on May 19, 2026

Town of Southampton Hotel Deals

The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
The price is CA $275 per night from May 27 to May 28
CA $275
CA $349 total
May 27 - May 28
includes taxes & fees
9.6/10 Exceptional! (503 reviews)
"Nice and clean"

Reviewed on May 24, 2026

The Bentley Hotel Southampton
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
The price is CA $532 per night from Jun 7 to Jun 8
CA $532
CA $608 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (617 reviews)
"What a quaint hotel/inn. Upon entering there is a nice front desk with the nicest people to help you. Right off of the reception area is a lovely breakfast lounge that over looks the harbor. The people there couldn't be nicer. The rooms are very clean and big enough so you don't feel cramped, unlike ..."

Reviewed on May 24, 2026

Sag Harbor Inn
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $210 per night from May 27 to May 28
CA $210
CA $275 total
May 27 - May 28
includes taxes & fees
7.2/10 Good! (996 reviews)
"Ac kept room cool"

Reviewed on May 17, 2026

The Atlantic Hotel
See all 2,024 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.
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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 $964. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.