$62 Cheap flights to Town of Southold Town

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Top places to visit in Town of Southold Town

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

Greenport
A calm lake with a forest in the background during sunset.
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Southold

Southold
A lighthouse on a rocky outcrop with a boat in the water.
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Orient

Orient

Cheap flights to Town of Southold Town from $62 One Way, $128 Round Trip

$128 return flights and $62 one-way flights to Town of Southold Town were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Dec 5 - Sat, Dec 12
MCO
Orlando
HVN
New Haven
$128 Roundtrip, found 7 hours ago
$128
Roundtrip
found 7 hours ago
Select Avelo Airlines flight, departing Sat, Dec 5 from Orlando to New Haven, returning Sat, Dec 12, priced at $128 found 7 hours ago
Tue, Dec 8 - Tue, Dec 8
MCO
Orlando
ISP
Islip
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando to Islip, returning Tue, Dec 8, priced at $130 found 5 days ago
Fri, Jan 8 - Mon, Jan 11
TPA
Tampa
HVN
New Haven
$130 Roundtrip, found 1 hour ago
$130
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa to New Haven, returning Mon, Jan 11, priced at $130 found 1 hour ago
Wed, Nov 18 - Sat, Dec 5
MCO
Orlando
HVN
New Haven
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Nov 18 from Orlando to New Haven, returning Sat, Dec 5, priced at $134 found 3 days ago
Tue, Dec 8 - Tue, Dec 15
MCO
Orlando
ISP
Islip
$138 Roundtrip, found 3 days ago
$138
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando to Islip, returning Tue, Dec 15, priced at $138 found 3 days ago
Fri, Jan 8 - Mon, Jan 11
TPA
Tampa
HVN
New Haven
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa to New Haven, returning Mon, Jan 11, priced at $139 found 1 hour ago
Wed, Nov 11 - Sat, Nov 14
MCO
Orlando
HVN
New Haven
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Nov 11 from Orlando to New Haven, returning Sat, Nov 14, priced at $139 just found
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando
HVN
New Haven
$145 Roundtrip, found 8 hours ago
$145
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando to New Haven, returning Sun, Dec 6, priced at $145 found 8 hours ago
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Find The Perfect Hotel For After Your Flight

Score Epic Town of Southold Town Accommodation Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$183 nightly
The price is $209 total per night from Nov 22 to Nov 23
$209 total
Nov 22 - Nov 23
Total with taxes and fees
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 ...
Opens in a new windowSound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$171 nightly
The price is $196 total per night from Nov 17 to Nov 18
$196 total
Nov 17 - Nov 18
Total with taxes and fees
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing ...
9.2/10 Wonderful! (440 reviews)
"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of ..."

Reviewed on Oct 27, 2026

Opens in a new windowZey Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
$154 nightly
The price is $176 total per night from Nov 17 to Nov 18
$176 total
Nov 17 - Nov 18
Total with taxes and fees
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 ...
Opens in a new windowThe Harbor Front Inn
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Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
$235 nightly
The price is $269 total per night from Nov 1 to Nov 2
$269 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this beach hotel in Greenport. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
10/10 Exceptional! (186 reviews)
"Nicely renovated and enjoyable."

Reviewed on Oct 28, 2026

Opens in a new windowSilver Sands Motel & Beach Bungalows
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.

Need a Car For After Your Flight?

Special

Managers Special
  • 4 people
  • Unlimited mileage
New York, New York, USA
Managers Special

$33

$104 total
found 1 day ago
Special Managers Special

Compact

Nissan Versa Note
  • 5 people
  • Unlimited mileage
New York, New York, USA
Nissan Versa Note

$39

$117 total
found 1 day ago
Compact Nissan Versa Note

Economy

Ford Fiesta
  • 5 people
  • Unlimited mileage
New York, New York, USA
Ford Fiesta

$39

$117 total
found 1 day ago
Economy Ford Fiesta

Standard

Volkswagen Jetta
  • 5 people
  • Unlimited mileage
New York City, New York, USA
Volkswagen Jetta

$42

$145 total
found 1 day ago
Standard Volkswagen Jetta

Town of Southold Town

When you plan to buy tickets for flights to Town of Southold Town, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

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Bargain Tickets for Town of Southold Town Flights

Orbitz offers deeply discounted flights to Town of Southold Town, and we provide the resources to research your travel destination and plan your complete itinerary.

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If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Town of Southold Town flights.

Frequently asked questions

Which airlines fly to Town of Southold Town?
Booking a flight to Town of Southold Town is easy — simply choose from 17 airlines that fly into MacArthur Airport (ISP). When you've finalized your sightseeing itinerary and packed your suitcase, these leading domestic carriers will welcome you on board:

  • Southwest Airlines - 73 flights to Town of Southold Town per month
  • Frontier Airlines - 38 flights to Town of Southold Town per month
  • Breeze Airways - 1 flights to Town of Southold Town per month

How much is a flight to Town of Southold Town?
Plenty of fantastic deals were up for the taking this week, with return flights to Town of Southold Town ranging from $128 to $145. But it was jet-setters beginning their trip from Tampa (TPA) who landed the really big bargains. One-way fares to Town of Southold Town started at just $62.
How to book the cheapest flight to Town of Southold Town?
Scoring cheap flights to Town of Southold Town is as simple as booking with Orbitz. But if you're eager to make sure you're walking away with the best flight deals around, here are some suggestions to follow:

  • Depending on where you're leaving from, choose the 'Nearby airports' function (located under the departure and arrival options). In some instances, other departure points will have cheaper fares.
  • Similarly, click on the 'Show flexible dates' option to bring up the airfares on days around your selected departure. You may be able to pick up cheaper flight deals if you're flexible with your schedule.
  • To filter your results, click on 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird gets the best savings, so purchase your seats once you've settled on your travel dates. The most affordable airfares are quick to go and prices normally climb as the departure date nears.
  • Save on your trip by bundling your hotel, flights and car rental into one convenient package deal. Your credit card will thank you.
  • Flying during the busy season can mean steep airfares. If possible, plan your trip outside of popular dates, such as Christmas, New Year's Eve and Easter.

What is the best time to book a flight to Town of Southold Town?
Book in January, February or August for the best flight prices to Town of Southold Town. Once you've found a bargain, snap it up — cheap flights tend to pop up and vanish at the tap of a button.
What day of the week is the cheapest to book a flight to Town of Southold Town?
If you're after low-cost fares to Town of Southold Town, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a fabulous flight deal will be all yours.
What is the cheapest day of the week to fly to Town of Southold Town?
You can grab cheap flights to Town of Southold Town by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is also more affordable, while Saturday has the most expensive ticket prices. Whether you prefer to stretch your travel budget or fly out on any day that's convenient, you'll always find a good deal with Orbitz.
What is the cheapest month to fly to Town of Southold Town?
Travel sometime in August if you don't want to eat into your budget. Orbitz data has found that it's generally the best month for cheap flights to Town of Southold Town. June is when fares are at their most expensive.
Which airlines allow free cancellation?
Flexibility is important these days, that's why Orbitz lets you search for flights that won't slap on fees for any amendments. Add your departure and arrival destinations, then click on "Filter by flexible change policies." We'll show you options that include free cancellation within 24 hours of booking and no change fees.
What do I need for the flight to Town of Southold Town?
There's so much to plan for any big journey, so it's nice to get some help before you set out. Here are a few suggestions to ensure you're prepared for departure:

  • Make sure you've got your travel papers and identification. For overseas trips, you'll need to take your passport. When booking your flights, always use the same details that are listed on your current ID.
  • Stock your carry-on bag with activities and snacks and you'll easily pass the time on your medium-haul flight. If you get the chance, join the airport's Wi-Fi and download your favorite podcast or playlist to your phone or tablet before take off.
  • Both air conditioning and high altitudes can create a cool environment. No matter what the weather is outside, pack a sweater to keep nice and warm during your flight.

How do I get cheap first-class/business deals to Town of Southold Town?
Experienced travelers have a way of finding business or first-class flights to Town of Southold Town that don't cost a packet. Be like them with these practical tips:

  • Be flexible with your travel dates and wait for huge sales on business or first-class airfares.
  • Many low-cost airlines offer excellent business or premium-class seating without the hefty fees.
  • Make the most of your airline's customer loyalty program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

What is the best time to go to Town of Southold Town?
Anytime is an awesome time to experience Town of Southold Town, though May, June and August are the busiest months. Like most of the Northern Hemisphere, summertime begins June 20. If you'd prefer to spend most of your days in a light T-shirt than a winter coat, this time of year would be ideal. Expect average daytime highs of 75 ºF and nightly lows around 70 ºF.
Travel tips for Town of Southold Town

  • Downtown Town of Southold Town has plenty of renowned attractions. Drawcards like Kontokosta Winery and 67 Steps Beach will keep your feet moving and your adventurous spirit happy.
  • You'll find fun day trip adventures a short commute from the center. Head for Yale University first and after that, Montauk Point Lighthouse.
  • When you want to explore other parts of Suffolk County, arrange a car rental and head in the direction of Northport. Islandia is another major city with loads to do and see.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.