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Southold

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Southold Flights as Low as $118

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 August, 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 $118, 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 $118 right now, why wait?

Southold Flight Information
Destination airport
LaGuardia
Destination airport IATA code
LGA
Roundtrip price
$118

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! (278 reviews)
"We had such a wonderful time, and the staff was incredibly helpful and attentive. We definitely recommend staying at the Sholas—it's a fantastic place!"

Reviewed on Jun 3, 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
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,005 reviews)
"Like most of the hotels in Ct. Old, but this clean and well maintained. I recommend it if you travel to This Ct shore area"

Reviewed on Jun 6, 2026

Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (1,005 reviews)
"Hotel is fine if you are just there for a night, maybe two, but the room, especially the carpet, need some major updates."

Reviewed on Jun 4, 2026

The Atlantic Hotel
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)
"The location and the amenities provided by the hotel was first classed"

Reviewed on May 27, 2026

Water's Edge Resort & Spa
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! (515 reviews)
"I loved My stay"

Reviewed on Jun 5, 2026

The Bentley Hotel Southampton
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
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! (315 reviews)
"The staff, James and Jessie were so pleasant and nice. We stay in the king bed suite and loved the private deck."

Reviewed on Jun 6, 2026

Zey Hotel
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! (653 reviews)
"Great"

Reviewed on Jun 1, 2026

Sound View Greenport
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.