Cheap Flights to Town of Southold Town (2026/2027)

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Greenport Harbour

Greenport

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Greenport
Aerial North Shore Long Island

Mattituck

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Mattituck

Best Town of Southold Town Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
2 bedroom luxury Empire State VIEW
2.0-star property

2 bedroom luxury Empire State VIEW

Jun 25 - Jun 27

2 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,776, price is now $1,551 per person
$1,551
per person
found 1 day ago
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Aug 7 - Aug 11

4 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was $3,010, price is now $1,653 per person
$1,653
per person
found 1 day ago
Loews Regency New York Hotel
5.0-star property

Loews Regency New York Hotel

Aug 20 - Aug 27

7 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $7,554, price is now $4,261 per person
$4,261
per person
found 16 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! (649 reviews)
"Room had a gorgeous view and the sauna was great but so over priced"

Reviewed on May 24, 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! (607 reviews)
"Wonderful, relaxing stay. Convenient to both train and ferry. Warm and inviting reception team."

Reviewed on May 28, 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! (307 reviews)
"Easy check in staff great very relaxing place and fantastic location. Will stay here again"

Reviewed on May 26, 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 . 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, 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 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 and . 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.