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Southold

Name: The Harbor Front Inn
Rating: 8.8

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Southold Flights as Low as $68

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

All deals

One way

Roundtrip

Fri, Jun 5 - Mon, Jun 8

ATL

Hartsfield-Jackson Atlanta Intl.

LGA

LaGuardia

$68

Roundtrip

found 7 hours ago

Fri, Jun 5 - Mon, Jun 8

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$73

Roundtrip

found 2 hours ago

Wed, May 13 - Thu, May 28

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$79

Roundtrip

found 15 hours ago

Wed, May 13 - Wed, May 27

ATL

Hartsfield-Jackson Atlanta Intl.

LGA

LaGuardia

$84

Roundtrip

found 3 hours ago

Sat, Aug 15 - Mon, Aug 17

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$88

Roundtrip

found 1 day ago

Wed, May 13 - Thu, May 28

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$94

Roundtrip

found 15 hours ago

Fri, Jun 5 - Sat, Jun 13

ATL

Hartsfield-Jackson Atlanta Intl.

LGA

LaGuardia

$95

Roundtrip

found 10 hours ago

Sat, Jun 6 - Mon, Jun 8

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$97

Roundtrip

found 14 hours ago

Thu, Aug 13 - Mon, Aug 17

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$98

Roundtrip

found 1 day ago

Wed, May 13 - Wed, May 27

ATL

Hartsfield-Jackson Atlanta Intl.

LGA

LaGuardia

$130

Roundtrip

found 3 hours ago

Wed, Jun 10 - Thu, Jun 11

ATL

Hartsfield-Jackson Atlanta Intl.

JFK

John F. Kennedy Intl.

$130

Roundtrip

found 14 hours ago

Wed, Jun 10 - Wed, Jun 10

ATL

Hartsfield-Jackson Atlanta Intl.

JFK

John F. Kennedy Intl.

$176

Roundtrip

found 14 hours ago

Thu, May 14 - Mon, May 18

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$177

Roundtrip

found 4 days ago

Wed, May 20 - Sun, May 31

ATL

Hartsfield-Jackson Atlanta Intl.

EWR

Newark Liberty Intl. Airport

$181

Roundtrip

just found

Thu, May 28 - Fri, May 29

ATL

Hartsfield-Jackson Atlanta Intl.

JFK

John F. Kennedy Intl.

$201

Roundtrip

found 1 day ago

Tue, May 5 - Thu, May 21

ATL

Hartsfield-Jackson Atlanta Intl.

HVN

Tweed - New Haven Regional

$239

Roundtrip

found 4 days 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 June, 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 $68, 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 $68 right now, why wait?

Southold Flight Information
Destination airport	LaGuardia
Destination airport IATA code	LGA
Roundtrip price	$67

Last Minute Hotel Deals in Southold

The Shoals Suites and Slips

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! (265 reviews)

My girlfriend and I stayed in April and it was amazing stay. Rooms are outstanding, one of the best rooms we ever stayed, and location was stunning. Beautiful marina, great waterfront views from the property. It was so quiet and relaxing. We went to Greenport for dinners. 10$ Breakfast cards were ...

Reviewed on Apr 25, 2026

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Vine & Sand

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

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Sound View Greenport

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! (639 reviews)

This is a lovely motel located right on the Sound and all rooms face the water. The room was clean and relatively spacious, though most of the space was devoted to the kitchen and living areas. The bathroom was a bit small, as was the sleeping area. My family, including an elderly relative, traveled ...

Reviewed on Apr 21, 2026

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The Bentley Hotel Southampton

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! (473 reviews)

The property was just as described and we couldn't have been more pleasantly surprised when we arrived after the long trek thru what seemed like nothingness between NYC and Southampton. At 1st glance we were a bit skeptical, but upon entry found the property ti be a hidden gem. We even extended our ...

Reviewed on Apr 26, 2026

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Sag Harbor Inn

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! (604 reviews)

Lovely hotel. Very clean, very friendly staff, great water pressure. Breakfast was continental... Fruit, cereal, yogurt, muffins. Fresh coffee. Overall nice experience.

Reviewed on Apr 26, 2026

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Water's Edge Resort & Spa

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! (1,001 reviews)

Was very nice used hotels.com saved alot for both rooms. Enkoyed the pool and spa hot tub was great. Pricy but worth it the view was beautiful

Reviewed on Apr 25, 2026

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Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

7.8/10 Good! (1,002 reviews)

I was first placed in a dirty room but they were very quick and efficient to move me which was great b/c I don’t like first floor rooms. In my second room on 2nd floor the window lock was broken so I couldn’t lock it. Uncomfortable but being in 2nd floor helped. Clock in the room nor working or unplugged?? ...

Reviewed on Apr 20, 2026

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The Harbor Front Inn

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! (592 reviews)

Great

Reviewed on Apr 23, 2026

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See all 4,424 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.

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