Flights To Town of Southold Town - Cheap Flights Starting at CA $82

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Greenport

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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.

Tue, Nov 3 - Wed, Nov 4
MCO
Orlando Intl.
ISP
MacArthur
CA $206 Roundtrip, found 2 days ago
CA $206
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Nov 3 from Orlando Intl. to MacArthur, returning Wed, Nov 4, priced at CA $206 found 2 days ago
Tue, Nov 3 - Wed, Nov 4
MCO
Orlando Intl.
ISP
MacArthur
CA $225 Roundtrip, found 2 days ago
CA $225
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Nov 3 from Orlando Intl. to MacArthur, returning Wed, Nov 4, priced at CA $225 found 2 days ago
Thu, Oct 29 - Sun, Nov 1
BWI
Baltimore Washington Intl. Thurgood Marshall
HVN
Tweed - New Haven Regional
CA $236 Roundtrip, found 5 days ago
CA $236
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Oct 29 from Baltimore Washington Intl. Thurgood Marshall to Tweed - New Haven Regional, returning Sun, Nov 1, priced at CA $236 found 5 days ago
Fri, Oct 30 - Mon, Nov 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $259 Roundtrip, found 1 day ago
CA $259
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Nov 2, priced at CA $259 found 1 day ago
Fri, Oct 30 - Mon, Nov 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $278 Roundtrip, found 1 day ago
CA $278
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Nov 2, priced at CA $278 found 1 day ago
Thu, Oct 22 - Sun, Oct 25
BWI
Baltimore Washington Intl. Thurgood Marshall
HVN
Tweed - New Haven Regional
CA $333 Roundtrip, found 1 day ago
CA $333
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Oct 22 from Baltimore Washington Intl. Thurgood Marshall to Tweed - New Haven Regional, returning Sun, Oct 25, priced at CA $333 found 1 day ago
Sun, Oct 18 - Thu, Oct 22
BWI
Baltimore Washington Intl. Thurgood Marshall
HVN
Tweed - New Haven Regional
CA $337 Roundtrip, found 5 days ago
CA $337
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Sun, Oct 18 from Baltimore Washington Intl. Thurgood Marshall to Tweed - New Haven Regional, returning Thu, Oct 22, priced at CA $337 found 5 days ago
Fri, Oct 30 - Sun, Nov 1
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $339 Roundtrip, found 1 day ago
CA $339
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Nov 1, priced at CA $339 found 1 day 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.
Royalton New York
4.0-star property

Royalton New York

Dec 11 - Dec 14

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was CA $2,071, price is now CA $1,244 per person
CA $1,244
per person
found 1 day ago
Lotte New York Palace
4.5-star property

Lotte New York Palace

Dec 27 - Dec 31

4 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was CA $3,541, price is now CA $1,816 per person
CA $1,816
per person
found 20 hours ago
The William Hotel Midtown, New York
3.5-star property

The William Hotel Midtown, New York

Dec 11 - Dec 14

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was CA $2,514, price is now CA $1,430 per person
CA $1,430
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 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 $206. 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, November 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 $206 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 $206 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.