Town of Southampton Vacation Packages

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

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Top vacation destinations in Town of Southampton

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Southampton

Southampton

Top Town of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Price was CA $1,281, price is now CA $816 per person
CA $816
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,761 reviews)
It was a very pleasant stay

Reviewed on Jun 17, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $5,544, price is now CA $2,435 per person
CA $2,435
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
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

Sofitel New York

Sofitel New York

4.5 out of 5
Manhattan
Price was CA $2,601, price is now CA $1,546 per person
CA $1,546
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,245 reviews)
Sheets gave my daughter skin rush

Reviewed on Jun 15, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,647, price is now CA $993 per person
CA $993
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,144 reviews)
The location is amazing. Near to the subway for a quick ride to Times Square. But everything you need in walking distance. Near to la guardia airport. Rooms are small but comfortable and have everything you need. I would stay here again.

Reviewed on Jun 20, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $11,276, price is now CA $6,912 per person
CA $6,912
per person
Sep 4 - Sep 12
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

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 $343 per night from Jul 6 to Jul 7
CA $343
CA $427 total
Jul 6 - Jul 7
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Do not stay here!! This place does not look like its photos."

Reviewed on Jun 20, 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 $650 per night from Jul 19 to Jul 20
CA $650
CA $778 total
Jul 19 - Jul 20
includes taxes & fees
9.6/10 Exceptional! (529 reviews)
"Ok stay, thank you."

Reviewed on Jun 20, 2026

The Bentley Hotel Southampton
The Hampton Maid

The Hampton Maid

2.5 out of 5
259 E Montauk Hwy Hampton Bays NY
9.2/10 Wonderful! (712 reviews)
"stayed with my boyfriend and we wished we stayed longer than one night! gorgeous little place. the rooms were spotless and the pool was so nice to lounge by! We will be staying again."

Reviewed on Jun 17, 2026

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The Hampton Maid
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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 $816. 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.