Flights To Town of Southold Town - Cheap Flights Starting at CA $87

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Greenport

Flights
Greenport

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.

Sat, Feb 27 - Wed, Mar 3
DJT
President Donald J. Trump Intl. Airport
HVN
Tweed - New Haven Regional
CA $187 Roundtrip, found 2 days ago
CA $187
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Feb 27 from President Donald J. Trump Intl. Airport to Tweed - New Haven Regional, returning Wed, Mar 3, priced at CA $187 found 2 days ago
Fri, Nov 13 - Sun, Nov 15
SRQ
Sarasota-Bradenton Intl.
ISP
MacArthur
CA $296 Roundtrip, found 14 hours ago
CA $296
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Fri, Nov 13 from Sarasota-Bradenton Intl. to MacArthur, returning Sun, Nov 15, priced at CA $296 found 14 hours ago
Sun, Nov 1 - Sat, Nov 14
DJT
President Donald J. Trump Intl. Airport
ISP
MacArthur
CA $390 Roundtrip, found 3 days ago
CA $390
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sun, Nov 1 from President Donald J. Trump Intl. Airport to MacArthur, returning Sat, Nov 14, priced at CA $390 found 3 days ago
Tue, Dec 1 - Thu, Dec 3
DJT
President Donald J. Trump Intl. Airport
ISP
MacArthur
CA $398 Roundtrip, found 4 days ago
CA $398
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Dec 1 from President Donald J. Trump Intl. Airport to MacArthur, returning Thu, Dec 3, priced at CA $398 found 4 days ago
Sun, Nov 1 - Sat, Nov 14
DJT
President Donald J. Trump Intl. Airport
ISP
MacArthur
CA $438 Roundtrip, found 3 days ago
CA $438
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sun, Nov 1 from President Donald J. Trump Intl. Airport to MacArthur, returning Sat, Nov 14, priced at CA $438 found 3 days ago
Sat, Feb 27 - Wed, Mar 3
DJT
President Donald J. Trump Intl. Airport
HVN
Tweed - New Haven Regional
CA $463 Roundtrip, found 2 days ago
CA $463
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Sat, Feb 27 from President Donald J. Trump Intl. Airport to Tweed - New Haven Regional, returning Wed, Mar 3, priced at CA $463 found 2 days ago
Fri, Oct 23 - Tue, Oct 27
DJT
President Donald J. Trump Intl. Airport
ISP
MacArthur
CA $489 Roundtrip, found 19 hours ago
CA $489
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Fri, Oct 23 from President Donald J. Trump Intl. Airport to MacArthur, returning Tue, Oct 27, priced at CA $489 found 19 hours ago
Sun, Nov 1 - Sat, Nov 14
DJT
President Donald J. Trump Intl. Airport
ISP
MacArthur
CA $503 Roundtrip, found 3 days ago
CA $503
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Nov 1 from President Donald J. Trump Intl. Airport to MacArthur, returning Sat, Nov 14, priced at CA $503 found 3 days ago
Sun, Oct 25 - Thu, Oct 29
YVR
Vancouver Intl.
ISP
MacArthur
CA $1,272 Roundtrip, found 5 days ago
CA $1,272
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sun, Oct 25 from Vancouver Intl. to MacArthur, returning Thu, Oct 29, priced at CA $1,272 found 5 days ago
Sun, Oct 25 - Thu, Oct 29
YVR
Vancouver Intl.
ISP
MacArthur
CA $1,389 Roundtrip, found 5 days ago
CA $1,389
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Oct 25 from Vancouver Intl. to MacArthur, returning Thu, Oct 29, priced at CA $1,389 found 5 days ago
Sun, Oct 25 - Thu, Oct 29
YVR
Vancouver Intl.
ISP
MacArthur
CA $1,414 Roundtrip, found 5 days ago
CA $1,414
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sun, Oct 25 from Vancouver Intl. to MacArthur, returning Thu, Oct 29, priced at CA $1,414 found 5 days ago
Price found within the past 48 hours. Click for updated prices.
Ink 48 Hotel
4.5-star property

Ink 48 Hotel

Dec 11 - Dec 18

7 night stay

Halifax (YHZ) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,801, price is now CA $2,416 per person
CA $2,416
per person
found 19 hours ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Dec 6 - Dec 10

4 night stay

Halifax (YHZ) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $4,276, price is now CA $2,539 per person
CA $2,539
per person
found 14 hours ago
1 Hotel Central Park
5.0-star property

1 Hotel Central Park

Dec 11 - Dec 18

7 night stay

Halifax (YHZ) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $8,943, price is now CA $5,542 per person
CA $5,542
per person
found 19 hours ago
Don't see what you're looking for?
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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 Hashamomuck Pond and Railroad Museum of Long Island are located nearby.
Opens in a new windowSound View Greenport
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.
Opens in a new windowZey Hotel
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.
9/10 Wonderful! (664 reviews)
"Breakfast was “why bother”. Insufficient light in our room and poorly placed."

Reviewed on Oct 7, 2026

Opens in a new windowThe Harbor Front Inn
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Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
Book a stay at this beach hotel in Greenport. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Railroad Museum of Long Island and East End Seaport Maritime Museum are located nearby.
10/10 Exceptional! (174 reviews)
"Unique and beautiful property"

Reviewed on Oct 5, 2026

Opens in a new windowSilver Sands Motel & Beach Bungalows
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 $187. 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, February 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 $187 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 $187 and CA $1,414. 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.