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Southold

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Southold Flights as Low as $121

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

Avelo Airlines
Fri, Sep 25 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$121 Roundtrip, found 5 hours ago
$121
Roundtrip
found 5 hours ago
Select Avelo Airlines flight, departing Fri, Sep 25 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $121 found 5 hours ago
Breeze Airways
Fri, Sep 25 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$168 Roundtrip, found 5 hours ago
$168
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $168 found 5 hours ago
Avelo Airlines
Fri, Sep 18 - Mon, Sep 21
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$171 Roundtrip, found 5 hours ago
$171
Roundtrip
found 5 hours ago
Select Avelo Airlines flight, departing Fri, Sep 18 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $171 found 5 hours ago
Breeze Airways
Fri, Sep 25 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$173 Roundtrip, found 5 hours ago
$173
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $173 found 5 hours ago
Breeze Airways
Fri, Sep 25 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$178 Roundtrip, found 5 hours ago
$178
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Sep 25 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $178 found 5 hours ago
Bargain Flight
Tue, Jan 12 - Tue, Jan 19
SAV
Savannah - Hilton Head Intl.
EWR
Newark Liberty Intl. Airport
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Jan 12 from Savannah - Hilton Head Intl. to Newark Liberty Intl. Airport, returning Tue, Jan 19, priced at $215 found 1 day ago
Bargain Flight
Fri, Dec 4 - Sun, Dec 6
JAX
Jacksonville Intl.
EWR
Newark Liberty Intl. Airport
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Dec 4 from Jacksonville Intl. to Newark Liberty Intl. Airport, returning Sun, Dec 6, priced at $222 found 1 day ago
Delta
Tue, Oct 20 - Sat, Oct 24
SAV
Savannah - Hilton Head Intl.
JFK
John F. Kennedy Intl.
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 20 from Savannah - Hilton Head Intl. to John F. Kennedy Intl., returning Sat, Oct 24, priced at $243 found 2 days ago
Frontier Airlines
Sat, Dec 5 - Mon, Dec 7
JAX
Jacksonville Intl.
EWR
Newark Liberty Intl. Airport
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Jacksonville Intl. to Newark Liberty Intl. Airport, returning Mon, Dec 7, priced at $257 found 3 days ago
American Airlines
Tue, Oct 20 - Sat, Oct 24
SAV
Savannah - Hilton Head Intl.
JFK
John F. Kennedy Intl.
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 20 from Savannah - Hilton Head Intl. to John F. Kennedy Intl., returning Sat, Oct 24, priced at $263 found 2 days ago
JetBlue Airways
Fri, Sep 25 - Tue, Sep 29
JAX
Jacksonville Intl.
JFK
John F. Kennedy Intl.
$278 Roundtrip, found 4 days ago
$278
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Sep 25 from Jacksonville Intl. to John F. Kennedy Intl., returning Tue, Sep 29, priced at $278 found 4 days ago
JetBlue Airways
Fri, Sep 25 - Tue, Sep 29
JAX
Jacksonville Intl.
JFK
John F. Kennedy Intl.
$291 Roundtrip, found 4 days ago
$291
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Sep 25 from Jacksonville Intl. to John F. Kennedy Intl., returning Tue, Sep 29, priced at $291 found 4 days ago
American Airlines
Wed, Nov 11 - Sat, Nov 14
JAX
Jacksonville Intl.
LGA
LaGuardia
$306 Roundtrip, found 1 day ago
$306
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Nov 11 from Jacksonville Intl. to LaGuardia, returning Sat, Nov 14, priced at $306 found 1 day ago
Delta
Fri, Dec 4 - Sun, Dec 6
SAV
Savannah - Hilton Head Intl.
LGA
LaGuardia
$359 Roundtrip, found 14 hours ago
$359
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Dec 4 from Savannah - Hilton Head Intl. to LaGuardia, returning Sun, Dec 6, priced at $359 found 14 hours ago
Southwest Airlines
Wed, Nov 11 - Sat, Nov 14
JAX
Jacksonville Intl.
LGA
LaGuardia
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 11 from Jacksonville Intl. to LaGuardia, returning Sat, Nov 14, priced at $363 found 1 day ago
Breeze Airways
Sun, Sep 20 - Mon, Sep 21
SAV
Savannah - Hilton Head Intl.
HVN
Tweed - New Haven Regional
$980 Roundtrip, found 5 hours ago
$980
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sun, Sep 20 from Savannah - Hilton Head Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $980 found 5 hours ago

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 September, 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 14 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 $121, 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 $121 right now, why wait?

Southold Flight Information
Destination airport
LaGuardia
Destination airport IATA code
LGA
Roundtrip price
$104

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! (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

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The Shoals Suites and Slips
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. ...
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Pier Blue Inn Old Saybrook - Essex
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! (725 reviews)
"Clean room, staff was lovely"

Reviewed on Sep 15, 2026

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Sound View Greenport
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! (1,002 reviews)
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."

Reviewed on Sep 12, 2026

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Water's Edge Resort & Spa
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 ...
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The Atlantic Hotel
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! (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

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Zey Hotel
Greenview Inn Riverhead

Greenview Inn Riverhead

2 out of 5
1433 W Main St Riverhead NY
Stay at this motel in Riverhead. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Splish Splash Water Park and Riverhead Raceway ...
7.4/10 Good! (868 reviews)
"We had a great stay here! Rooms were updated and everything was new and very clean. I would definitely stay here again if we’re in the area!"

Reviewed on Sep 15, 2026

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Greenview Inn Riverhead
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
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

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North Fork Resort
See all 4,302 properties in Southold
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.