Town of Southampton Vacation Packages

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Top vacation destinations in Town of Southampton

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Top Town of Southampton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on Aug. 6, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Oct 18 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very Good! (544 reviews)
Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread to the pool area. July is expensive but it was definitely worth it. We live on Long Island and didn't have to deal with flying issues. Just a 2 hour drive and 4 days of relaxing sun.....

Reviewed on Aug. 5, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

The Manner, The Unbound Collection by Hyatt

The Manner, The Unbound Collection by Hyatt

5 out of 5
Manhattan
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (36 reviews)
The lounge area is super cozy and relaxing.

Reviewed on Aug. 4, 2025

ModernHaus SoHo

ModernHaus SoHo

4.5 out of 5
Manhattan
per person
Sep 17 - Sep 26
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
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Reviewed on Jul. 2, 2025

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 $346 per night from Aug 17 to Aug 18
CA $346
CA $430 total
Aug 17 - Aug 18
includes taxes & fees
7/10 Good! (892 reviews)
"Great Budget friendly hotel without sacrificing on amenities and comfort would definitely go back again no problem"

Reviewed on Aug. 4, 2025

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 $303 per night from Sep 3 to Sep 4
CA $303
CA $385 total
Sep 3 - Sep 4
includes taxes & fees
9.4/10 Exceptional! (303 reviews)
Hamptons
"The room was totally renovated and very comfortable, you would not expect this since the outside looks dated but inside is beautiful!"

Reviewed on Aug. 1, 2025

The Bentley Hotel Southampton
Baron's Cove

Baron's Cove

4 out of 5
31 West Water Street, Sag Harbor, NY
The price is CA $581 per night from Sep 4 to Sep 5
CA $581
CA $731 total
Sep 4 - Sep 5
includes taxes & fees
9/10 Wonderful! (276 reviews)
"We treated ourselves to room service one rainy night and it was great. The housekeeping staff was attentive and professional, one young woman offered to help get my bag upstairs! Super location for my needs of daily Tracy Anderson studio work Lovely spot"

Reviewed on Jul. 29, 2025

Baron's Cove
See all 1,886 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 $1,107. 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.