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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.

Reviewed on Aug. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,736, price is now CA $2,074 per person
CA $2,074
per person
Oct 28 - Oct 31
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Luxury Collection Hotel Manhattan Midtown

The Luxury Collection Hotel Manhattan Midtown

5 out of 5
Manhattan
Price was CA $1,798, price is now CA $1,101 per person
CA $1,101
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Great location, complimentary water which saved us a lot of money on bottled water! Front desk hooked us up with an upgrade. We requested to have all snacks and drinks removed from our son's room and they didn't do it. He got into the snacks and we were charged $160 super annoying, we knew he would get into the snacks and would have appreciated them doing us a solid by removing the $20 gummy bears

Reviewed on Aug. 17, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,572, price is now CA $974 per person
CA $974
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
This hotel had a beautiful view of the Hudson and the city. It was super convenient to the PATH station and parking garage.

Reviewed on Aug. 25, 2025

Hotel Hendricks

Hotel Hendricks

4 out of 5
Manhattan
Price was CA $3,303, price is now CA $2,096 per person
CA $2,096
per person
Oct 31 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,638 reviews)
We had a fantastic stay at Hotel Hendricks for 4 nights during our stay in New York. Location: Great! It is 5 minute walk to the subway station and walkable to Times Square in 10 minutes. Location felt safe to walk to and from even at night. Staff: Amazing- always helpful. Swift check in and always helpful if you needed something. The Room: Our room was lovely and so quiet. It had great air con and the shower was incredible! The bed was also super comfortable. The room amenities were good- shower gel, shampoo and conditioner all in the shower. Body lotion and soap were plentiful. Cleaning was done every day to a high standard. Overall, we really enjoyed our stay and would stay again if we were to revisit New York.

Reviewed on Aug. 25, 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 $223 per night from Sep 21 to Sep 22
CA $223
CA $289 total
Sep 21 - Sep 22
includes taxes & fees
7/10 Good! (915 reviews)
"Nice staff and the hotel is fine."

Reviewed on Aug. 24, 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 $310 per night from Sep 3 to Sep 4
CA $310
CA $394 total
Sep 3 - Sep 4
includes taxes & fees
9.4/10 Exceptional! (324 reviews)
"The hotel is located in a central part of Southampton, with most attractions within 5–10 miles. It’s clean, well-kept, and the room was spacious and well-equipped. Unfortunately, the service—specifically from Joseph—was disappointing. Upon arrival, I was mistaken for a delivery person, which felt ..."

Reviewed on Aug. 25, 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 $559 per night from Sep 22 to Sep 23
CA $559
CA $703 total
Sep 22 - Sep 23
includes taxes & fees
8.8/10 Excellent! (284 reviews)
"Barons Cove Inn is very well located i.e. walkable to pretty much everything. It’s also charming, somewhat quirky, clean, comfortable, has very nice room amenities and internet access, a friendly attentive staff, a nice bar and restaurant, a lovely pool, is waterfront and has a great front porch ..."

Reviewed on Aug. 11, 2025

Baron's Cove
See all 1,869 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 $697. 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.