$50 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 $50 One Way, $110 Round Trip

$110 return flights and $50 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.

Thu, Dec 3 - Thu, Dec 10
MCO
Orlando
ISP
Islip
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando to Islip, returning Thu, Dec 10, priced at $110 found 3 hours ago
Thu, Jan 14 - Sun, Jan 17
MCO
Orlando
HVN
New Haven
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jan 14 from Orlando to New Haven, returning Sun, Jan 17, priced at $125 found 3 days ago
Tue, Sep 29 - Tue, Oct 6
MCO
Orlando
ISP
Islip
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Sep 29 from Orlando to Islip, returning Tue, Oct 6, priced at $136 found 1 day ago
Tue, Sep 29 - Wed, Sep 30
MCO
Orlando
ISP
Islip
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Sep 29 from Orlando to Islip, returning Wed, Sep 30, priced at $139 found 2 days ago
Wed, Sep 30 - Wed, Sep 30
MCO
Orlando
ISP
Islip
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando to Islip, returning Wed, Sep 30, priced at $140 found 2 days ago
Thu, Dec 10 - Mon, Dec 14
MCO
Orlando
HVN
New Haven
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando to New Haven, returning Mon, Dec 14, priced at $142 found 3 days ago

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
$259 nightly
The price is $296 total per night from Oct 1 to Oct 2
$296 total
Oct 1 - Oct 2
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
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$227 nightly
The price is $256 total per night from Oct 1 to Oct 2
$256 total
Oct 1 - Oct 2
Total with taxes and fees
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 ...
9.4/10 Exceptional! (334 reviews)
"Our room was clean and very spacious, the bathroom was large and modern. They setup a food shed outside with a nice menu and bar where you can sit down and have fresh oysters for example and a drink when returning from the wineries all day. The staff outside was super friendly. However, here are ..."

Reviewed on Sep 2, 2026

Opens in a new windowThe Shoals Suites and Slips
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$169 nightly
The price is $193 total per night from Sep 23 to Sep 24
$193 total
Sep 23 - Sep 24
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! (401 reviews)
"Such an amazing hotel to stay for the weekend"

Reviewed on Sep 9, 2026

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
$249 nightly
The price is $284 total per night from Oct 4 to Oct 5
$284 total
Oct 4 - Oct 5
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 Special

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

$82

$232 total
found 3 days ago
Economy Special Managers Special

Compact SUV

Chevrolet Trax
  • 5 people
  • Unlimited mileage
New York, New York, USA
Chevrolet Trax

$83

$226 total
found 3 days ago
Compact SUV Chevrolet Trax

Midsize

Kia K4
  • 5 people
  • Unlimited mileage
New York, New York, USA
Kia K4

$84

$238 total
found 3 days ago
Midsize Kia K4

Fullsize

Nissan Altima
  • 5 people
  • Unlimited mileage
New York, New York, USA
Nissan Altima

$88

$248 total
found 3 days ago
Fullsize Nissan Altima
Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.

Town of Southold Town

Why search for low cost fares on your flights to Town of Southold Town when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Town of Southold Town

Orbitz offers massive discounts and substantial last-minute savings on your Town of Southold Town flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Town of Southold Town flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Town of Southold Town. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Town of Southold Town but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

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 $110 to $142. 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 $50.
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.