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Southold

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Southold Flights as Low as $76

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 May, 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 $76, 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 $76 right now, why wait?

Southold Flight Information
Destination airport
Newark Liberty Intl. Airport
Destination airport IATA code
EWR
Roundtrip price
$70

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
The price is $291 per night from Apr 20 to Apr 21
$291
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (156 reviews)
"Fantastic. The room was very comfortable with a kitchen area and large bathroom. There are boat slips outside and a view of the water."

Reviewed on Apr 14, 2025

The Shoals Suites and Slips
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is $212 per night from May 6 to May 7
$212
includes taxes & fees
May 6 - May 7
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,003 reviews)
"Staff is always very receptive and cordial!"

Reviewed on Apr 10, 2025

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is $91 per night from Apr 19 to Apr 20
$91
includes taxes & fees
Apr 19 - Apr 20
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. ...
7.6/10 Good! (943 reviews)
"the property was close to the ocean. very pet friendly and accommodated our needs well"

Reviewed on Apr 12, 2025

Pier Blue Inn Old Saybrook - Essex
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
The price is $169 per night from Apr 30 to May 1
$169
includes taxes & fees
Apr 30 - May 1
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
Hyatt Riverhead NY
"Bed was sooo comfortable, the heated pool was great and the breakfast buffet was great as well!"

Reviewed on Apr 15, 2025

Hyatt Place Long Island East End
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
The price is $313 per night from Apr 20 to Apr 21
$313
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (226 reviews)
"Excellent stay while visiting our son!"

Reviewed on Apr 10, 2025

Baron's Cove
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
The price is $143 per night from May 6 to May 7
$143
includes taxes & fees
May 6 - May 7
Stay at this 3-star 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! (933 reviews)
"The staff at this property were great across the board. The room was more space than we had anticipated and very convenient for everything we wanted to do in the area!"

Reviewed on Apr 16, 2025

Residence Inn by Marriott New York Long Island East End
The Harbor Front Inn
The Harbor Front Inn
3.5 out of 5
209 Front St, Greenport, NY
The price is $222 per night from Apr 27 to Apr 28
$222
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (451 reviews)
2 day getaway
"The experience was very good. everything was what I expected. only thought was the $25 parking was a bit much"

Reviewed on Apr 15, 2025

The Harbor Front Inn
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is $375 per night from Apr 21 to Apr 22
$375
includes taxes & fees
Apr 21 - Apr 22
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,003 reviews)
"It was a quiet time of the year(off season) , remodel of the pool area was nice."

Reviewed on Apr 13, 2025

Saybrook Point Resort & Marina
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.