Cheap Flights to Town of Southold Town from $48 (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.

Wed, Sep 30 - Wed, Oct 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Wed, Sep 30 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Oct 7, priced at $96 found 2 days ago
Wed, Aug 26 - Wed, Sep 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $98 found 2 days ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 3 days ago
$102
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at $102 found 3 days ago
Thu, Sep 3 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$109 Roundtrip, found 2 hours ago
$109
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at $109 found 2 hours ago
Wed, Aug 12 - Wed, Aug 19
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 19, priced at $112 found 1 day ago
Wed, Sep 16 - Wed, Sep 23
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 3 days ago
$114
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Sep 16 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 23, priced at $114 found 3 days ago
Sat, Sep 5 - Sun, Sep 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 1 hour ago
$114
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $114 found 1 hour ago
Sat, Sep 5 - Sat, Sep 5
MCO
Orlando Intl.
ISP
MacArthur
$115 Roundtrip, found 7 hours ago
$115
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Orlando Intl. to MacArthur, returning Sat, Sep 5, priced at $115 found 7 hours ago

Best Town of Southold Town Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel
4.0-star property

Radio Hotel

Sep 10 - Sep 14

4 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,202, price is now $615 per person
$615
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Aug 12 - Aug 17

5 night stay

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Frontier Airlines • Roundtrip • Coach
Price was $1,497, price is now $775 per person
$775
per person
found 1 day ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Sep 29 - Oct 2

3 night stay

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,215, price is now $636 per person
$636
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! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

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.
9.2/10 Wonderful! (344 reviews)
"We absolutely adored the Zey hotel. What a gem in the very heart of Greenport! Super clean and comfortable. All the staff were welcoming and accommodating. Eclectic design was so refreshing and fun. We highly recommend Zey hotel and look forward to staying there in the future. Thank you for making ..."

Reviewed on Jul 8, 2026

Opens in a new windowZey Hotel
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! (292 reviews)
"Had an amazing stay here during the off season with our newborn. The room was clean and grounds were beautifully maintained. Can’t wait to come back here this summer to see the property in full action."

Reviewed on Jul 8, 2026

Opens in a new windowThe Shoals Suites and Slips
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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.
9.4/10 Exceptional! (30 reviews)
"Overall the stay was pleasant. The cottages are well maintained. This property is still developing so there was active construction. It listed some amenities that were not yet available and some that were only available through a weekend stay which we did not have with a Sunday-Tuesday booking. I ..."

Reviewed on Jul 8, 2026

Opens in a new windowNorth Fork Resort
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 $96. 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, September 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 $96 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 $96 and $115. 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.