Cheap Flights to Town of Southold Town from $50 (2026/2027)

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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.

Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $100 found 1 day ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 3 days ago
$111
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $111 found 3 days ago
Sat, Sep 26 - Mon, Sep 28
MCO
Orlando Intl.
ISP
MacArthur
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando Intl. to MacArthur, returning Mon, Sep 28, priced at $112 just found
Sat, Sep 26 - Tue, Sep 29
MCO
Orlando Intl.
ISP
MacArthur
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando Intl. to MacArthur, returning Tue, Sep 29, priced at $114 just found
Sat, Oct 3 - Tue, Oct 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 6 days ago
$114
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Sat, Oct 3 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Oct 6, priced at $114 found 6 days ago
Wed, Sep 2 - Wed, Sep 9
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$115 Roundtrip, found 3 days ago
$115
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Sep 2 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 9, priced at $115 found 3 days ago
Thu, Dec 10 - Mon, Dec 14
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Dec 14, priced at $118 found 4 days ago
Wed, Sep 2 - Wed, Sep 9
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Sep 2 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 9, priced at $120 found 3 days ago

Best Town of Southold Town Flight and Hotel Packages

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!

Sep 3 - Sep 6

3 night stay

Atlanta (ATL) to New Haven (HVN)

Frontier Airlines • Roundtrip • Coach
Price was $2,295, price is now $1,077 per person
$1,077
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Sep 24 - Sep 27

3 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was $3,276, price is now $1,739 per person
$1,739
per person
found 1 day ago
Seven Beach Lane
2.0-star property

Seven Beach Lane

Oct 15 - Oct 20

5 night stay

San Juan (SJU) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,284, price is now $1,225 per person
$1,225
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
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' Market are located nearby.
9.6/10 Exceptional! (50 reviews)
"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."

Reviewed on Aug 20, 2026

Opens in a new windowNorth Fork Resort
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! (384 reviews)
"The room was clean and very large. There is parking in the rear of the hotel."

Reviewed on Aug 22, 2026

Opens in a new windowZey Hotel
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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! (323 reviews)
"Amazing stay!!!"

Reviewed on Aug 21, 2026

Opens in a new windowThe Shoals Suites and Slips
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 $100. 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, December 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 $100 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 $100 and $120. 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.
How long is the average flight to Town of Southold Town?
The length of a direct flight to Town of Southold Town can vary, but here are the average airborne times for some top routes:

  • Orlando, FL (MCO-Orlando Intl.) to MacArthur Airport (ISP) - 2 hours and 36 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to MacArthur Airport (ISP) - 1 hour and 6 minutes
  • Tampa, FL (TPA-Tampa Intl.) to MacArthur Airport (ISP) - 2 hours and 46 minutes

What can I expect on a flight to Town of Southold Town?
Factors including the airline you choose and where your plane takes off from will mostly determine your onboard experience. You're likely to find all sorts of flights to Town of Southold Town, from cheap flights for family vacations to premium airfares. Warm meals, entertainment and games for the youngsters are a taste of what most airlines offer on long-haul services.