Flights To Town of Southold Town - Cheap Flights Starting at CA $76

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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.

Thu, Sep 17 - Thu, Sep 24
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $140 Roundtrip, found 5 days ago
CA $140
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 17 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Sep 24, priced at CA $140 found 5 days ago
Sat, Sep 5 - Sun, Sep 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $154 Roundtrip, found 3 days ago
CA $154
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at CA $154 found 3 days ago
Wed, Jul 1 - Mon, Aug 31
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $192 Roundtrip, found 1 day ago
CA $192
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Jul 1 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 31, priced at CA $192 found 1 day ago
Thu, Jun 4 - Sun, Jun 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $200 Roundtrip, found 2 days ago
CA $200
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jun 7, priced at CA $200 found 2 days ago
Thu, Jul 30 - Thu, Aug 6
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $209 Roundtrip, found 5 days ago
CA $209
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Jul 30 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Aug 6, priced at CA $209 found 5 days ago
Thu, Jul 9 - Sun, Jul 12
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $212 Roundtrip, found 3 hours ago
CA $212
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 12, priced at CA $212 found 3 hours ago
Fri, Jul 10 - Sun, Jul 12
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $215 Roundtrip, found 3 hours ago
CA $215
Roundtrip
found 3 hours ago
Select Avelo Airlines flight, departing Fri, Jul 10 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Jul 12, priced at CA $215 found 3 hours ago
Thu, Sep 17 - Thu, Sep 24
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $233 Roundtrip, found 5 days ago
CA $233
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Sep 17 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Sep 24, priced at CA $233 found 5 days ago
Wed, Jul 8 - Tue, Jul 14
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,331 Roundtrip, found 12 hours ago
CA $1,331
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, Jul 8 from Pearson Intl. to MacArthur, returning Tue, Jul 14, priced at CA $1,331 found 12 hours ago
Tue, Jul 21 - Sun, Jul 26
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,350 Roundtrip, found 2 days ago
CA $1,350
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 21 from Pearson Intl. to MacArthur, returning Sun, Jul 26, priced at CA $1,350 found 2 days ago
Tue, Jul 21 - Sun, Jul 26
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,351 Roundtrip, found 2 days ago
CA $1,351
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 21 from Pearson Intl. to MacArthur, returning Sun, Jul 26, priced at CA $1,351 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
New York Marriott Marquis
4.5-star property

New York Marriott Marquis

Jun 30 - Jul 3

3 night stay

Buffalo (BUF) to Newark Liberty Intl. Airport (EWR)

American Airlines • Coach

Newark Liberty Intl. Airport (EWR) to Buffalo (BUF)

Delta • Coach
Price was CA $1,559, price is now CA $891 per person
CA $891
per person
found 1 day ago
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Jul 12 - Jul 15

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $3,309, price is now CA $1,745 per person
CA $1,745
per person
found 1 day ago
Topping Rose House
4.5-star property

Topping Rose House

Jun 23 - Jun 26

3 night stay

Calgary (YYC) to Newark Liberty Intl. Airport (EWR)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $7,608, price is now CA $4,644 per person
CA $4,644
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! (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! (605 reviews)
"Close to everything in town. Breakfast was great! Rooms were very clean and well stocked."

Reviewed on May 26, 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 CA $140. 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 $140 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 $140 and CA $1,351. 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.