Flights To Town of Southold Town - Cheap Flights Starting at CA $65

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Greenport Harbour

Greenport

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Greenport
beach of east marion seen from water side

East Marion

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East Marion

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

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

Wed, Jun 24 - Wed, Jul 1
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $145 Roundtrip, found 1 day ago
CA $145
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Jun 24 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Jul 1, priced at CA $145 found 1 day ago
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $148 Roundtrip, found 4 hours ago
CA $148
Roundtrip
found 4 hours ago
Select Avelo Airlines flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Jun 24, priced at CA $148 found 4 hours ago
Fri, Jul 31 - Mon, Aug 3
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $149 Roundtrip, found 4 days ago
CA $149
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 31 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Aug 3, priced at CA $149 found 4 days ago
Mon, Jul 13 - Thu, Jul 16
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $197 Roundtrip, found 1 day ago
CA $197
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Jul 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, Jul 16, priced at CA $197 found 1 day ago
Fri, Jul 31 - Mon, Aug 3
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $198 Roundtrip, found 4 days ago
CA $198
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Fri, Jul 31 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Aug 3, priced at CA $198 found 4 days ago
Thu, Jun 25 - Thu, Jul 2
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $211 Roundtrip, found 1 day ago
CA $211
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Jun 25 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, Jul 2, priced at CA $211 found 1 day ago
Tue, Jun 2 - Fri, Jun 5
RDU
Raleigh - Durham Intl.
ISP
MacArthur
CA $212 Roundtrip, found 4 days ago
CA $212
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Jun 2 from Raleigh - Durham Intl. to MacArthur, returning Fri, Jun 5, priced at CA $212 found 4 days ago
Wed, Aug 19 - Wed, Aug 26
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
CA $248 Roundtrip, found 5 days ago
CA $248
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Wed, Aug 19 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Wed, Aug 26, priced at CA $248 found 5 days ago
Tue, Jul 21 - Sun, Jul 26
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,350 Roundtrip, found 1 day ago
CA $1,350
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 21 from Pearson Intl. to MacArthur, returning Sun, Jul 26, priced at CA $1,350 found 1 day ago
Tue, Jul 21 - Sun, Jul 26
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,351 Roundtrip, found 1 day ago
CA $1,351
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 21 from Pearson Intl. to MacArthur, returning Sun, Jul 26, priced at CA $1,351 found 1 day ago
Tue, Jul 21 - Sun, Jul 26
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,359 Roundtrip, found 1 day ago
CA $1,359
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 21 from Pearson Intl. to MacArthur, returning Sun, Jul 26, priced at CA $1,359 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Jul 12 - Jul 15

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $3,309, price is now CA $1,745 per person
CA $1,745
per person
found 2 hours ago
2 bedroom luxury Empire State VIEW
2.0-star property

2 bedroom luxury Empire State VIEW

Jul 10 - Jul 15

5 night stay

Toronto (YYZ) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $8,918, price is now CA $4,035 per person
CA $4,035
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Jun 18 - Jun 21

3 night stay

Toronto (YYZ) to New York (JFK)

Air Canada • Roundtrip • Coach
Price was CA $4,272, price is now CA $2,552 per person
CA $2,552
per person
found 1 day ago
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Travelers ❤️ These Town of Southold Town 🏨

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Railroad Museum of Long Island and The Old Field Vineyards are located nearby.
8.4/10 Very Good! (649 reviews)
"Room had a gorgeous view and the sauna was great but so over priced"

Reviewed on May 24, 2026

Opens in a new windowSound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenport Carousel and Camera Obscura are located nearby.
8.8/10 Excellent! (604 reviews)
"Location was great. The balcony overlooking the water and boardwalk was a big benefit."

Reviewed on May 25, 2026

Opens in a new windowThe Harbor Front Inn
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions The Old Field Vineyards and Crescent Beach are located nearby.
9.4/10 Exceptional! (271 reviews)
"Great a accomodation"

Reviewed on May 22, 2026

Opens in a new windowThe Shoals Suites and Slips
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Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing Company and Greenport Farmers' Market are located nearby.
9.2/10 Wonderful! (306 reviews)
"A small hotel with a vibrant and eclectic decor, ample common spaces for relaxing and socializing and a great location for strolling through Greenport. My wife and I stayed for two nights and agreed that we would stay here again were we to return to the area. Hotel staff accommodated our somewhat ..."

Reviewed on May 23, 2026

Opens in a new windowZey Hotel
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 Southold Town?
Based on prices found over the last seven days on Travelocity, a roundtrip flight to Town of Southold Town was as low as CA $145. If you can be flexible with your dates, it's easier to land a great bargain. This price was available on Travelocity for flights to Town of Southold Town 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 Southold Town?
If you're planning a vacation in Town of Southold Town, June is the cheapest time to hop on a plane. This is based on Travelocity's direct return flight demand from January to December last year. Work out your travel dates and lock in your spot today.
How can I check my flight status to Town of Southold Town?
There are a couple of useful ways to track your flight status. You'll discover all the necessary details in our "Trips" portal, which is located at the top of our homepage. Sign in or create a new account in seconds — you can then access and manage your bookings whenever you please. For those on the move, the Travelocity app can also help you look up the status of your flight to Town of Southold Town, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Town of Southold Town?
Being flexible with your travel dates will help you grab a sensational deal. Travelocity makes it easy to find your perfect fare through the "Flexible dates" feature. First, search for your Town of Southold Town flight, then compare prices for surrounding days by clicking the Flexible dates dropdown box above. Booking well in advance and avoiding peak travel periods are other ways to save some cash. In the last seven days, the cheapest price for a return flight to Town of Southold Town was CA $145 on our site. 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 Southold Town with Travelocity?
From cheap flights to Town of Southold Town to rental cars, activities and more, Travelocity is your one-stop shop for exciting adventures. With everything you need in one convenient place, you can enjoy more time thinking about the wonderful things that await you in Town of Southold Town and less time on travel planning. Plus with our Price Match Guarantee and 24/7 customer support, our goal is to make your next getaway a magical one.
What are the most popular flight routes to Town of Southold Town?
Check out these leading flight routes to Town of Southold Town and start organizing you next amazing adventure:

  • Orlando, FL (MCO-Orlando Intl.) to MacArthur Airport (ISP) - 589 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to MacArthur Airport (ISP) - 368 flights a month.
  • Tampa, FL (TPA-Tampa Intl.) to MacArthur Airport (ISP) - 216 flights a month.

How much is a flight to Town of Southold Town on average?
In the last seven days, roundtrip flights to Town of Southold Town were priced between CA $145 and CA $1,359. No matter your bank balance, we have some incredible deals to help you stick within budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.