$51 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 $51 One Way, $88 Round Trip

$88 return flights and $51 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, Oct 17 - Sat, Oct 24
MCO
Orlando
ISP
Islip
$88 Roundtrip, found 11 hours ago
$88
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Orlando to Islip, returning Sat, Oct 24, priced at $88 found 11 hours ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando
HVN
New Haven
$106 Roundtrip, found 2 days ago
$106
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando to New Haven, returning Sun, Jan 31, priced at $106 found 2 days ago
Fri, Oct 30 - Sat, Oct 31
MCO
Orlando
ISP
Islip
$109 Roundtrip, found 4 days ago
$109
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Oct 30 from Orlando to Islip, returning Sat, Oct 31, priced at $109 found 4 days ago
Thu, Dec 3 - Thu, Dec 10
MCO
Orlando
ISP
Islip
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando to Islip, returning Thu, Dec 10, priced at $110 found 5 days ago
Sat, Oct 10 - Sat, Oct 17
MCO
Orlando
ISP
Islip
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Orlando to Islip, returning Sat, Oct 17, priced at $111 found 1 day ago
Sat, Oct 10 - Sun, Oct 18
MCO
Orlando
ISP
Islip
$119 Roundtrip, found 5 days ago
$119
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Orlando to Islip, returning Sun, Oct 18, priced at $119 found 5 days ago
Fri, Jan 29 - Mon, Feb 1
TPA
Tampa
HVN
New Haven
$140 Roundtrip, found 20 hours ago
$140
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Fri, Jan 29 from Tampa to New Haven, returning Mon, Feb 1, priced at $140 found 20 hours ago
Fri, Dec 4 - Mon, Dec 7
TPA
Tampa
HVN
New Haven
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 4 from Tampa to New Haven, returning Mon, Dec 7, priced at $149 found 1 day ago
Thu, Jan 7 - Sun, Jan 10
TPA
Tampa
HVN
New Haven
$157 Roundtrip, found 16 hours ago
$157
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Thu, Jan 7 from Tampa to New Haven, returning Sun, Jan 10, priced at $157 found 16 hours ago
Fri, Dec 4 - Mon, Dec 7
TPA
Tampa
HVN
New Haven
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 4 from Tampa to New Haven, returning Mon, Dec 7, priced at $157 found 1 day ago
Fri, Jan 22 - Sun, Jan 31
TPA
Tampa
HVN
New Haven
$158 Roundtrip, found 14 hours ago
$158
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Fri, Jan 22 from Tampa to New Haven, returning Sun, Jan 31, priced at $158 found 14 hours ago
Thu, Jan 28 - Sun, Jan 31
TPA
Tampa
HVN
New Haven
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Tampa to New Haven, returning Sun, Jan 31, priced at $159 found 2 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
$248 nightly
The price is $284 total per night from Oct 1 to Oct 2
$284 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 ...
8.4/10 Very Good! (726 reviews)
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."

Reviewed on Sep 15, 2026

Opens in a new windowSound View Greenport
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 29 to Sep 30
$193 total
Sep 29 - Sep 30
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! (402 reviews)
"My Husband Phil & I had the Best Stay. Very Quaint Hotel, just a couple of blocks from waterfront.Absolutely spotless, so many sitting areas, Coffee, tea water and ice available 24-7. Our room was spotless, decorated so well. We also had a balcony. James and all staff were so Pleasant and so accommodating. ..."

Reviewed on Sep 14, 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
$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! (339 reviews)
"Our stay was filled with quietness set in a backdrop of beautiful blue skies enveloping the peconic bay. What a great place to come apart and forget about the stress of the week, relax and unwind. My husband and I were pleased with our stay. Everyone was ao friendly and helpful Mario was very attentive ..."

Reviewed on Sep 14, 2026

Opens in a new windowThe Shoals Suites and Slips
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North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
$278 nightly
The price is $318 total per night from Sep 16 to Sep 17
$318 total
Sep 16 - Sep 17
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' ...
9.6/10 Exceptional! (55 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"

Reviewed on Sep 14, 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.

Need a Car For After Your Flight?

Mini Van

Chrysler Pacifica
  • 7 people
  • Unlimited mileage
New York City, New York, USA
Chrysler Pacifica

$45

$258 total
found 2 days ago
Mini Van Chrysler Pacifica

Special

Mystery Car May Be Gas Hybrid or EV
  • 4 people
  • Unlimited mileage
Jamaica, New York, USA
Mystery Car May Be Gas Hybrid or EV

$48

$136 total
found 2 days ago
Special Mystery Car May Be Gas Hybrid or EV

Premium Pickup Regular Cab

Ford F150
  • 5 people
  • Unlimited mileage
New York City, New York, USA
Ford F150

$54

$303 total
found 2 days ago
Premium Pickup Regular Cab Ford F150

Compact

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

$57

$166 total
found 1 day ago
Compact Nissan Versa Note
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

Town of Southold Town

Start your search for cheap flights to Town of Southold Town on Orbitz. Orbitz is where you will discover guaranteed low prices on Town of Southold Town flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Town of Southold Town flights. You can also review and reserve hotel rooms for when your Town of Southold Town flights land and see other special offers.

Low Prices Guaranteed on Flights to Town of Southold Town

Orbitz offers large discounts on a wide range of Town of Southold Town flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Town of Southold Town while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Town of Southold Town to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Town of Southold Town. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

Frequently asked questions

Which airlines fly to Town of Southold Town?
Booking a flight to Town of Southold Town is easy — simply choose from 24 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 $88 to $159. 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 $51.
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.