Flights To Town of Southold Town - Cheap Flights Starting at CA $86

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An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport

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Greenport
A coastal landscape with a sandy beach, calm water, and scattered trees.

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.

Tue, Sep 15 - Tue, Sep 29
MCO
Orlando Intl.
ISP
MacArthur
CA $157 Roundtrip, found 2 days ago
CA $157
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Sep 15 from Orlando Intl. to MacArthur, returning Tue, Sep 29, priced at CA $157 found 2 days ago
Fri, Oct 2 - Mon, Oct 5
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $190 Roundtrip, found 5 days ago
CA $190
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Oct 2 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Oct 5, priced at CA $190 found 5 days ago
Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $209 Roundtrip, found 16 hours ago
CA $209
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at CA $209 found 16 hours ago
Fri, Oct 2 - Mon, Oct 5
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $212 Roundtrip, found 5 days ago
CA $212
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Oct 2 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Oct 5, priced at CA $212 found 5 days ago
Tue, Sep 15 - Tue, Sep 29
MCO
Orlando Intl.
ISP
MacArthur
CA $216 Roundtrip, found 2 days ago
CA $216
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Sep 15 from Orlando Intl. to MacArthur, returning Tue, Sep 29, priced at CA $216 found 2 days ago
Tue, Sep 15 - Tue, Sep 29
MCO
Orlando Intl.
ISP
MacArthur
CA $224 Roundtrip, found 2 days ago
CA $224
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 15 from Orlando Intl. to MacArthur, returning Tue, Sep 29, priced at CA $224 found 2 days ago
Fri, Sep 25 - Mon, Sep 28
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $228 Roundtrip, found 6 days ago
CA $228
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 25 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at CA $228 found 6 days ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $229 Roundtrip, found 4 days ago
CA $229
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at CA $229 found 4 days ago
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
2.0-star property

Seven Beach Lane

Oct 4 - Oct 10

6 night stay

Toronto (YYZ) to New York (JFK)

Delta • Coach

New York (JFK) to Toronto (YYZ)

American Airlines • Coach
Price was CA $2,472, price is now CA $1,535 per person
CA $1,535
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Oct 2 - Oct 5

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $3,274, price is now CA $1,649 per person
CA $1,649
per person
found 1 day ago
Mandarin Oriental, New York
5.0-star property

Mandarin Oriental, New York

Aug 27 - Aug 30

3 night stay

Toronto (YTO) to New York (JFK)

Delta • Roundtrip • Coach
Price was CA $3,690, price is now CA $2,276 per person
CA $2,276
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.
8.4/10 Very good! (703 reviews)
"The property is well maintained and the location is perfect, however, there were some downsides during our stay. My fiancé, our dog, and I went to this hotel as it's a pet-friendly location, on their website they advertised amenities for pets (i.e, Yeti dog bowl(s), plush bed) but we never received ..."

Reviewed on Aug 24, 2026

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! (386 reviews)
"Staff was accommodating and kind. The coffee and tea is a nice touch. Great location and nice common areas. Free parking. The room was a little shoddy, especially the bathroom but products were nice. They really need to dilute the cleaning products though. Way too strong of a smell in the linens ..."

Reviewed on Aug 24, 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! (326 reviews)
"Beautiful spacious rooms with great rocking chairs on the balcony with a water view. Property was immaculate. Lovely continental breakfast. Great outdoor food truck for a snack and adult beverage!"

Reviewed on Aug 25, 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 CA $157. 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 CA $157 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 $157 and CA $229. 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.