$64 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 $64 One Way, $125 Round Trip

$125 return flights and $64 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.

Tue, Dec 8 - Tue, Dec 8
MCO
Orlando
ISP
Islip
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando to Islip, returning Tue, Dec 8, priced at $125 found 2 hours ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando
HVN
New Haven
$128 Roundtrip, found 21 hours ago
$128
Roundtrip
found 21 hours ago
Select Avelo Airlines flight, departing Sat, Dec 5 from Orlando to New Haven, returning Sat, Dec 12, priced at $128 found 21 hours ago
Tue, Dec 8 - Tue, Dec 8
MCO
Orlando
ISP
Islip
$135 Roundtrip, found 2 hours ago
$135
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando to Islip, returning Tue, Dec 8, priced at $135 found 2 hours ago
Tue, Dec 8 - Tue, Dec 15
MCO
Orlando
ISP
Islip
$137 Roundtrip, found 18 hours ago
$137
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando to Islip, returning Tue, Dec 15, priced at $137 found 18 hours ago
Wed, Nov 11 - Sat, Nov 14
MCO
Orlando
HVN
New Haven
$139 Roundtrip, found 6 hours ago
$139
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Wed, Nov 11 from Orlando to New Haven, returning Sat, Nov 14, priced at $139 found 6 hours ago
Tue, Dec 8 - Tue, Dec 15
MCO
Orlando
ISP
Islip
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando to Islip, returning Tue, Dec 15, priced at $142 found 5 days 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
$181 nightly
The price is $207 total per night from Nov 22 to Nov 23
$207 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
$162 nightly
The price is $185 total per night from Oct 27 to Oct 28
$185 total
Oct 27 - Oct 28
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! (438 reviews)
"Had a nice stay. Room was very clean. Amenities were nice. We enjoyed our 40th anniversary."

Reviewed on Oct 24, 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
$168 nightly
The price is $192 total per night from Nov 22 to Nov 23
$192 total
Nov 22 - Nov 23
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 ...
9/10 Wonderful! (668 reviews)
"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue ..."

Reviewed on Oct 19, 2026

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
$230 nightly
The price is $262 total per night from Nov 1 to Nov 2
$262 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! (181 reviews)
"Everything was immaculate and staff were fantastic. Lots of small details that made the stay especially lovely."

Reviewed on Oct 23, 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

Dealers Choice
  • 4 people
  • Unlimited mileage
New York, New York, USA
Dealers Choice

$36

$110 total
found 1 day ago
Special Dealers Choice

Economy

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

$37

$113 total
found 1 day ago
Economy Ford Fiesta

Compact

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

$38

$113 total
found 1 day ago
Compact Nissan Versa Note

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
New York, New York, USA
Toyota Corolla

$39

$116 total
found 1 day ago
Midsize Toyota Corolla

Town of Southold Town

Orbitz is your one stop for guaranteed low prices on Town of Southold Town flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Town of Southold Town and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Town of Southold Town Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Town of Southold Town from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $125 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 $64.
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.