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Southold

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Southold Flights as Low as $56

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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Cheap Flights to Southold

Fall in love at first flight with your vacation to Southold by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Southold on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Southold, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Southold

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Southold with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the LGA airport.

What is the cheapest month to fly to Southold?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Southold are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Southold?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Southold.

What airport is best to fly into Southold?

When you’re planning your trip to Southold, convenience is the name of the game. Luckily, Southold East Hampton Airport is nearby so you can deplane and get going on checking off everything on your Southold must-do list.

How much are flights to Southold?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Southold on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $56, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Southold?

The trick to saving a stack of cash on your flight to Southold? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $56 right now, why wait?

Southold Flight Information
Destination airport
LaGuardia
Destination airport IATA code
LGA
Roundtrip price
$58

Last Minute Hotel Deals in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
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! (255 reviews)
Beautiful property near a picturesque town. I would definitely recommend. I’d love to return soon!

Reviewed on Apr 5, 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!

Reviewed on Mar 22, 2026

Vine & Sand
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
Enjoyable stay.

Reviewed on Mar 28, 2026

Water's Edge Resort & Spa
Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3 out of 5
2012 Old Country Road Riverhead NY
Book a stay at this business-friendly hotel in Riverhead. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
9/10 Wonderful! (1,003 reviews)
Ok

Reviewed on Apr 5, 2026

Residence Inn by Marriott New York Long Island East End
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
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! (627 reviews)
Really enjoyed our stay at the soundview. You are able to easily hear neighbors so just an FYI. Love being so close to the water and hearing the water and waves at night. Overnight oats at breakfast were my favorite.

Reviewed on Apr 2, 2026

Sound View Greenport
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (457 reviews)
Spacious suite. Wish our stay was longer. Very clean, lots of special touches. Great staff.

Reviewed on Apr 2, 2026

The Bentley Hotel Southampton
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street Riverhead NY
Book a stay at this business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
Did not use

Reviewed on Mar 27, 2026

Hyatt Place Long Island East End
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
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 ...
8.8/10 Excellent! (580 reviews)
Room was excellent and the beds were very comfortable. We went just prior to the season start so things were very calm. If i was to take issue with one thing; it would have been the shower was cool and never got hot. Not cold...but could have been warmer.

Reviewed on Apr 3, 2026

The 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.