Flights To Town of Southold Town - Cheap Flights Starting at CA $101

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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.

Sat, Jun 6 - Wed, Jun 10
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
CA $190 Roundtrip, just found
CA $190
Roundtrip
just found
Select Avelo Airlines flight, departing Sat, Jun 6 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Wed, Jun 10, priced at CA $190 just found
Fri, May 29 - Mon, Jun 1
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
CA $234 Roundtrip, found 2 days ago
CA $234
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, May 29 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Jun 1, priced at CA $234 found 2 days ago
Thu, Aug 27 - Mon, Aug 31
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
CA $241 Roundtrip, found 4 days ago
CA $241
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Thu, Aug 27 from Palm Beach Intl. to Tweed - New Haven Regional, returning Mon, Aug 31, priced at CA $241 found 4 days ago
Fri, May 29 - Mon, Jun 1
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
CA $244 Roundtrip, found 2 days ago
CA $244
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, May 29 from Palm Beach Intl. to Tweed - New Haven Regional, returning Mon, Jun 1, priced at CA $244 found 2 days ago
Sat, Jun 6 - Wed, Jun 10
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
CA $254 Roundtrip, just found
CA $254
Roundtrip
just found
Select Avelo Airlines flight, departing Sat, Jun 6 from Palm Beach Intl. to Tweed - New Haven Regional, returning Wed, Jun 10, priced at CA $254 just found
Fri, Jun 5 - Mon, Jun 8
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
CA $282 Roundtrip, found 2 days ago
CA $282
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Palm Beach Intl. to Tweed - New Haven Regional, returning Mon, Jun 8, priced at CA $282 found 2 days ago
Fri, Jun 5 - Mon, Jun 8
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
CA $293 Roundtrip, found 2 days ago
CA $293
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, Jun 5 from Palm Beach Intl. to Tweed - New Haven Regional, returning Mon, Jun 8, priced at CA $293 found 2 days ago
Fri, Jun 5 - Mon, Jun 8
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
CA $306 Roundtrip, found 2 days ago
CA $306
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 5 from Palm Beach Intl. to Tweed - New Haven Regional, returning Mon, Jun 8, priced at CA $306 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Sofitel New York
4.5-star property

Sofitel New York

Aug 9 - Aug 14

5 night stay

Winnipeg (YWG) to Newark Liberty Intl. Airport (EWR)

Air Canada • Non-stop • Coach

Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)

Delta • Non-stop • Coach
Price was CA $2,823, price is now CA $1,866 per person
CA $1,866
per person
found 23 hours ago
Mandarin Oriental, New York
5.0-star property

Mandarin Oriental, New York

Jun 10 - Jun 13

3 night stay

Toronto (YYZ) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $5,088, price is now CA $3,089 per person
CA $3,089
per person
found 1 day ago
Seven Beach Lane
2.0-star property

Seven Beach Lane

Jul 9 - Jul 13

4 night stay

Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)

Porter Airlines • Roundtrip • Coach
Price was CA $3,576, price is now CA $2,387 per person
CA $2,387
per person
found 20 hours 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! (648 reviews)
"They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty."

Reviewed on May 11, 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! (603 reviews)
"Friendly staff clean rooms and very nice views of the harbor. Breakfast was a nice touch. Will stay again."

Reviewed on May 22, 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 $190. 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 $190 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 $190 and CA $306. 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.