Search Cheap Flights to
Middletown

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Middletown Flights as Low as $150

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

Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 6 days ago
$150
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $150 found 6 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $154 found 2 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $154 found 6 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$155 Roundtrip, found 6 days ago
$155
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $155 found 6 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $159 found 2 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $159 found 1 day ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 6 days ago
$160
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $160 found 6 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $164 found 2 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $164 found 1 day ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$165 Roundtrip, found 5 days ago
$165
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $165 found 5 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $169 found 1 day ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $174 found 1 day ago
Breeze Airways
Thu, Jun 12 - Mon, Jun 16
MCO
Orlando Intl.
SWF
Stewart Intl.
$177 Roundtrip, found 23 hours ago
$177
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Thu, Jun 12 from Orlando Intl. to Stewart Intl., returning Mon, Jun 16, priced at $177 found 23 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $179 found 3 days ago
Fly Play
Thu, Jun 5 - Sun, Jun 15
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$446 Roundtrip, found 4 days ago
$446
Roundtrip
found 4 days ago
Select Fly Play flight, departing Thu, Jun 5 from Roissy-Charles de Gaulle to Stewart Intl., returning Sun, Jun 15, priced at $446 found 4 days ago
Breeze Airways
Sun, Jun 8 - Thu, Jun 12
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$529 Roundtrip, found 3 days ago
$529
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Jun 8 from Raleigh - Durham Intl. to Stewart Intl., returning Thu, Jun 12, priced at $529 found 3 days ago

Cheap Flights to Middletown

Fall in love at first flight with your vacation to Middletown 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 Middletown on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Middletown, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Middletown

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Middletown 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 POU airport.

What is the cheapest month to fly to Middletown?

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 Middletown are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Middletown?

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 Middletown.

What airport is best to fly into Middletown?

When you’re planning your trip to Middletown, convenience is the name of the game. Luckily, Middletown Stewart Intl. Airport is nearby so you can deplane and get going on checking off everything on your Middletown must-do list.

How much are flights to Middletown?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Middletown on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $150, 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 Middletown?

The trick to saving a stack of cash on your flight to Middletown? 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 $150 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$150

Last Minute Hotel Deals in Middletown

La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
3 out of 5
551 Route 211 E, Middletown, NY
Stay at this 3-star business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (701 reviews)
"I like that it was convenient with food and having the mall near by"

Reviewed on May 27, 2025

Get rates
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,003 reviews)
"Everything"

Reviewed on May 29, 2025

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Sleep Inn & Suites Middletown - Goshen
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
Stay at this 3-star hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (897 reviews)
Friendly and quiet
"Clean, good water pressure, plenty of hot water, friendly and quiet."

Reviewed on May 23, 2025

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Courtyard by Marriott Middletown Goshen
Hampton Inn by Hilton Middletown
Hampton Inn by Hilton Middletown
2.5 out of 5
20 Crystal Run Crossing, Middletown, NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,005 reviews)
"Staff at front desk was very nice and helpful. Room was clean and Hugh! When we asked for handicapped shower chair it was delivered immediately."

Reviewed on May 23, 2025

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Hampton Inn by Hilton Middletown
Super 8 by Wyndham Middletown
Super 8 by Wyndham Middletown
2.5 out of 5
563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.2/10 (1,000 reviews)
"Quick and friendly"

Reviewed on May 24, 2025

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Super 8 by Wyndham Middletown
Home2 Suites by Hilton Middletown
Home2 Suites by Hilton Middletown
3 out of 5
600 Route 211 East, Middletown, NY
Stay at this 3-star business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (685 reviews)
"Great"

Reviewed on May 19, 2025

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Home2 Suites by Hilton Middletown
Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
2 out of 5
19 Crystal Run Crossing, Middletown, NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7/10 Good! (999 reviews)
"Convenient location off highway and near Legoland. It’s set near walkable restaurants too."

Reviewed on May 2, 2025

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Microtel Inn & Suites by Wyndham Middletown
Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown Goshen
3 out of 5
57 TOWER DRIVE, Middletown, NY
Stay at this 3-star business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (294 reviews)
"Pool area great, clean and friendly staff, good complimentary breakfast and close to dining options"

Reviewed on May 5, 2025

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Residence Inn by Marriott Middletown Goshen
See all 1,428 properties in Middletown
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.