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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.

Frontier Airlines
Frontier Airlines
Breeze Airways
Breeze Airways
Breeze Airways
Frontier Airlines
Frontier Airlines
Breeze Airways
Breeze Airways
Breeze Airways
United
Delta
JetBlue Airways
American Airlines
American Airlines
Avelo Airlines

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 October, 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 16 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
$113

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! (269 reviews)
Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend.

Reviewed on May 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
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)
Great place very inexpensive.

Reviewed on May 16, 2026

Pier Blue Inn Old Saybrook - Essex
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! (499 reviews)
Amazing. Loved everything about this place and will be back. The rooms were surprisingly spacious and the decor was perfect. I wish the pool was opened but I guess only for true summer. A great value and we will be back.

Reviewed on May 16, 2026

The Bentley Hotel Southampton
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! (647 reviews)
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.

Reviewed on May 11, 2026

Sound View Greenport
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
Book a stay at this business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (614 reviews)
Nice room and view

Reviewed on May 15, 2026

Sag Harbor Inn
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! (1,006 reviews)
Bedding was suboptimal and toilets clogged. Additionally, very noisy due to 2 weddings in the resort that night… so not very relaxing.

Reviewed on May 17, 2026

Water's Edge Resort & Spa
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! (598 reviews)
the rooms were clean. Staff as nice and helpful. i would stay again.

Reviewed on May 16, 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.