$48 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 $48 One Way, $98 Round Trip

$98 return flights and $48 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.

Wed, Aug 26 - Wed, Sep 2
MCO
Orlando
HVN
New Haven
$98 Roundtrip, found 3 hours ago
$98
Roundtrip
found 3 hours ago
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando to New Haven, returning Wed, Sep 2, priced at $98 found 3 hours ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando
HVN
New Haven
$107 Roundtrip, found 19 hours ago
$107
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando to New Haven, returning Tue, Sep 8, priced at $107 found 19 hours ago
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando
HVN
New Haven
$111 Roundtrip, found 7 hours ago
$111
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando to New Haven, returning Sun, Dec 13, priced at $111 found 7 hours ago
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando
HVN
New Haven
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Sat, Sep 5, priced at $112 found 1 day ago
Sat, Sep 5 - Sun, Sep 6
MCO
Orlando
HVN
New Haven
$112 Roundtrip, found 21 hours ago
$112
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando to New Haven, returning Sun, Sep 6, priced at $112 found 21 hours ago
Wed, Oct 7 - Wed, Oct 14
MCO
Orlando
HVN
New Haven
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Oct 7 from Orlando to New Haven, returning Wed, Oct 14, priced at $114 just found
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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
$382 nightly
The price is $436 total per night from Aug 18 to Aug 19
$436 total
Aug 18 - Aug 19
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
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
$372 nightly
The price is $425 total per night from Jul 28 to Jul 29
$425 total
Jul 28 - Jul 29
Total with taxes and fees
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' ...
9.4/10 Exceptional! (35 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"

Reviewed on Jul 24, 2026

Opens in a new windowNorth Fork Resort
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$243 nightly
The price is $278 total per night from Aug 6 to Aug 7
$278 total
Aug 6 - Aug 7
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 ...
Opens in a new windowZey Hotel
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The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
$408 nightly
The price is $466 total per night from Aug 19 to Aug 20
$466 total
Aug 19 - Aug 20
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
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?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Town of Southold Town

Get the absolute lowest prices on flights to Town of Southold Town by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Town of Southold Town Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Town of Southold Town flights.

Avoid Check-In Hassles When Traveling On Flights to Town of Southold Town

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Town of Southold Town flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Town of Southold Town flight using Orbitz.

Frequently asked questions

Which airlines fly to Town of Southold Town?
Booking a flight to Town of Southold Town is easy — simply choose from 12 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 $98 to $114. But it was jet-setters beginning their trip from Orlando (MCO) who landed the really big bargains. One-way fares to Town of Southold Town started at just $48.
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.