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.
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Southampton

Southampton

Top Town of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $2,279, price is now CA $1,450 per person
CA $1,450
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (244 reviews)
The property was absolutely beautiful- so well decorated! The staff was not only helpful and knowledgeable, but also very kind. If you’re looking for a beautiful luxury property, definitely don’t sleep on this one!

Reviewed on Jul 2, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $3,721, price is now CA $1,910 per person
CA $1,910
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.4/10 Good! (3,239 reviews)
The room was clean the air conditioning was perfect at 60 degrees and the heater (hubby is anemic)was perfect at H2. The front desk staff was courteous, polite and professional. The eateries in the area McDonald's, the Chinese Restaurant and the Pizzeria are over priced and the food was not that good. There is a deli on the corner of 93rd Street is reasonably priced and the sandwiches and salads were delicious. I can't comment on parking because we took a taxi and public transportation. Overall we had a good time and a nice experience.

Reviewed on Jul 9, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $2,872, price is now CA $1,537 per person
CA $1,537
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (685 reviews)
Great location, great view

Reviewed on Jul 5, 2026

The Wall Street Inn

The Wall Street Inn

3 out of 5
Manhattan
Price was CA $4,196, price is now CA $2,475 per person
CA $2,475
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
Lovely spot convenient to the activities we were doing. Very friendly and helpful stuff.

Reviewed on Jul 5, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,493, price is now CA $2,239 per person
CA $2,239
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 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 $356 per night from Jul 26 to Jul 27
CA $356
CA $442 total
Jul 26 - Jul 27
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"Terrible!!!! We arrived at the Atlantic Inn at 5:00 pm after being on the beach all day only to be told that they cancelled our reservation for the 2 rooms we booked!!! They were so rude about it and didn’t even apologize. They tried running our credit card prior to arrival but unfortunately that ..."

Reviewed on Jul 5, 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 $424 per night from Jul 14 to Jul 15
CA $424
CA $519 total
Jul 14 - Jul 15
includes taxes & fees
9.6/10 Exceptional! (544 reviews)
"Great place to stay. I enjoyed it very much. Clean and friendly staff"

Reviewed on Jun 30, 2026

The Bentley Hotel Southampton
Budget Host East End

Budget Host East End

2 out of 5
30 Lake Avenue Riverhead NY
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Jul 15 to Jul 16
CA $177
CA $202 total
Jul 15 - Jul 16
includes taxes & fees
6.8/10 (832 reviews)
"My five-year-old and I arrived at the hotel around 6 PM. The hotel's location in Flanders/Riverhead offers convenient access to both Main Street (East and West) and the Riverside Walkway. While these are attractive features, it is important to note that the immediate vicinity remains somewhat questionable, ..."

Reviewed on Jul 8, 2026

Budget Host East End
See all 1,966 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 $1,450. 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 $268
per adult
Full Day Private Long Island Wine Tours from New York City
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

CA $1,845
per traveller
100% of travellers recommend
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,845
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.