Flights To Town of Southampton - Cheap Flights Starting at CA $363

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A coastal landscape with a sandy beach, a forested area, and a golf course.

Riverhead

Flights
Riverhead

How Much Does it Cost To Fly To Town of Southampton?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Nov 25 - Sat, Nov 28
BOS
Logan Intl.
ISP
MacArthur
CA $722 Roundtrip, found 1 day ago
CA $722
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to MacArthur, returning Sat, Nov 28, priced at CA $722 found 1 day ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $731 Roundtrip, found 23 hours ago
CA $731
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $731 found 23 hours ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $816 Roundtrip, found 23 hours ago
CA $816
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $816 found 23 hours ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $857 Roundtrip, found 23 hours ago
CA $857
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $857 found 23 hours ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $893 Roundtrip, found 23 hours ago
CA $893
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $893 found 23 hours ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $900 Roundtrip, found 23 hours ago
CA $900
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $900 found 23 hours ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $942 Roundtrip, found 23 hours ago
CA $942
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $942 found 23 hours ago
Thu, Sep 3 - Mon, Sep 7
BOS
Logan Intl.
ISP
MacArthur
CA $952 Roundtrip, found 23 hours ago
CA $952
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Thu, Sep 3 from Logan Intl. to MacArthur, returning Mon, Sep 7, priced at CA $952 found 23 hours ago
Fri, Sep 18 - Mon, Sep 21
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,200 Roundtrip, found 3 days ago
CA $1,200
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to MacArthur, returning Mon, Sep 21, priced at CA $1,200 found 3 days ago
Fri, Sep 18 - Mon, Sep 21
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,208 Roundtrip, found 3 days ago
CA $1,208
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to MacArthur, returning Mon, Sep 21, priced at CA $1,208 found 3 days ago
Mon, Sep 14 - Mon, Sep 21
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,213 Roundtrip, found 6 days ago
CA $1,213
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Mon, Sep 14 from Pearson Intl. to MacArthur, returning Mon, Sep 21, priced at CA $1,213 found 6 days ago
Price found within the past 48 hours. Click for updated prices.
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 15 - Oct 19

4 night stay

Toronto (YYZ) to New Haven (HVN)

Air Canada • Roundtrip • Coach
Price was CA $4,142, price is now CA $1,855 per person
CA $1,855
per person
found 4 hours ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Oct 7 - Oct 11

4 night stay

Toronto (YTO) to New York (JFK)

Delta • Coach

New York (JFK) to Toronto (YTO)

American Airlines • Coach
Price was CA $4,895, price is now CA $2,672 per person
CA $2,672
per person
found 1 day ago
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Oct 19 - Oct 23

4 night stay

Toronto (YTO) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $5,322, price is now CA $3,264 per person
CA $3,264
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Town of Southampton
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Travelers ❤️ These Town of Southampton 🏨

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Cooper's Beach and Sebonack Golf Course are located nearby.
Opens in a new windowThe Atlantic Hotel
Hampton's Vacation Inn

Hampton's Vacation Inn

2.5 out of 5
177 West Montauk Highway Hampton Bays NY
Stay at this guesthouse in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Regal UA Hampton Bays and Good Ground Park are located nearby.
Opens in a new window Hampton's Vacation Inn
Budget Host East End

Budget Host East End

2 out of 5
30 Lake Avenue Riverhead NY
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Splish Splash Water Park and All Star Bowling are located nearby.
6.8/10 (864 reviews)
"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front ..."

Reviewed on Aug 21, 2026

Opens in a new windowBudget Host East End
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The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cooper's Beach and Sebonack Golf Course are located nearby.
9.6/10 Exceptional! (563 reviews)
"The Bentley in Southampton is a great place to stay. The room is exceptionally clean and the beds are super comfortable. The staff are friendly and helpful. We always enjoy our stay and highly recommend!"

Reviewed on Aug 21, 2026

Opens in a new windowThe Bentley Hotel 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.

Frequently asked questions

How much is the cheapest flight to Town of Southampton?
The next vacation you take doesn't have to make a huge dent in your finances. Within the last seven days, the cheapest roundtrip flight to Town of Southampton cost CA $722. Find a good deal and spend the dollars you save on awesome experiences. This price was available on Travelocity for flights to Town of Southampton departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Town of Southampton?
Leave November free in your calendar, because it's the cheapest month to jet out to Town of Southampton. That's according to Travelocity's direct flight demand between January and December last year. With the cash you save, you can go on a shopping binge, go to a fancy restaurant or do something special.
How can I check my flight status to Town of Southampton?
"Trips" will clue you in when it comes to the finer details of your flight to Town of Southampton. Our convenient customer portal allows you to arrange everything from one place, from checking your flight status to making updates to your itinerary. Click on Trips at the top right of the Travelocity homepage and then sign in to your account or create a new one. You can also download the Travelocity app and access your info on the go. Whether you have the family flying with you or you're on your own, all your travel plans are right at your fingertips.
How do I find the best deals on flights to Town of Southampton?
Here are our tips — book early, avoid peak season and be flexible with your travel dates. If you don't have a specific date in mind, search for your flight to Town of Southampton on Travelocity and click on "Flexible dates" above your results. This will show you any cheaper tickets on surrounding days. CA $722 was the most affordable price for a roundtrip flight to Town of Southampton in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Town of Southampton with Travelocity?
An awesome break is just a click or two away when you arrange your trip with Travelocity. With great deals on cheap family flights, hotels, activities and more, we make it simple to find awesome prices to suit your needs. You can also try out our 24/7 customer assistance and free cancellations on most hotels throughout your trip. Wander wisely with us and secure your cheap flights to Town of Southampton today.
How much is a flight to Town of Southampton on average?
Roundtrip flights to Town of Southampton on our site cost between CA $722 and CA $1,213 in the last seven days. When you spot a plane fare that fits your budget, snap it up quick. Cheap deals don't stick around forever! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.