Flights To Town of Southold Town - Cheap Flights Starting at CA $121

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Town of Southold Town's top cities

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

Greenport

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

East Marion

Flights
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.

Fri, Sep 18 - Sun, Sep 20
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $220 Roundtrip, found 3 days ago
CA $220
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Sep 18 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Sep 20, priced at CA $220 found 3 days ago
Fri, Sep 11 - Sun, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
CA $235 Roundtrip, found 5 days ago
CA $235
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at CA $235 found 5 days ago
Fri, Jul 31 - Mon, Aug 10
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
CA $290 Roundtrip, found 3 days ago
CA $290
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Jul 31 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Mon, Aug 10, priced at CA $290 found 3 days ago
Fri, Sep 18 - Sun, Sep 20
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $327 Roundtrip, found 3 days ago
CA $327
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 18 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Sep 20, priced at CA $327 found 3 days ago
Fri, Sep 18 - Sun, Sep 20
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $331 Roundtrip, found 3 days ago
CA $331
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 18 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Sep 20, priced at CA $331 found 3 days ago
Sat, Jul 25 - Sat, Aug 1
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $337 Roundtrip, found 10 hours ago
CA $337
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Sat, Jul 25 from Tampa Intl. to Tweed - New Haven Regional, returning Sat, Aug 1, priced at CA $337 found 10 hours ago
Tue, Jul 21 - Sat, Jul 25
TPA
Tampa Intl.
ISP
MacArthur
CA $380 Roundtrip, found 22 hours ago
CA $380
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Tue, Jul 21 from Tampa Intl. to MacArthur, returning Sat, Jul 25, priced at CA $380 found 22 hours ago
Fri, Sep 18 - Sun, Sep 20
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $396 Roundtrip, found 3 days ago
CA $396
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 18 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Sep 20, priced at CA $396 found 3 days ago
Sat, Jul 25 - Fri, Jul 31
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,260 Roundtrip, found 6 days ago
CA $1,260
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 25 from Pearson Intl. to MacArthur, returning Fri, Jul 31, priced at CA $1,260 found 6 days ago
Sat, Jul 25 - Fri, Jul 31
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,268 Roundtrip, found 6 days ago
CA $1,268
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 25 from Pearson Intl. to MacArthur, returning Fri, Jul 31, priced at CA $1,268 found 6 days ago
Sat, Jul 25 - Fri, Jul 31
YYZ
Pearson Intl.
ISP
MacArthur
CA $1,301 Roundtrip, found 6 days ago
CA $1,301
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 25 from Pearson Intl. to MacArthur, returning Fri, Jul 31, priced at CA $1,301 found 6 days ago
Price found within the past 48 hours. Click for updated prices.
Hotel St. James
3.0-star property

Hotel St. James

Aug 19 - Aug 25

6 night stay

Detroit (DTW) to New York (JFK)

American Airlines • Roundtrip • Coach
Price was CA $1,804, price is now CA $1,058 per person
CA $1,058
per person
found 1 day ago
Night Hotel Broadway
3.0-star property

Night Hotel Broadway

Sep 18 - Sep 25

7 night stay

Toronto (YTO) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $3,721, price is now CA $1,910 per person
CA $1,910
per person
found 13 hours ago
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Aug 27 - Aug 30

3 night stay

Ottawa (YOW) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Price was CA $3,038, price is now CA $1,807 per person
CA $1,807
per person
found 3 hours ago
Don't see what you're looking for?
See all available trips from Detroit to Town of Southold Town
View all trips

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! (346 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 CA $220. 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 $220 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 $220 and CA $1,301. 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.