Search Cheap Flights to
Middletown

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Middletown Flights as Low as $206

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

Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 2 hours ago
$206
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $206 found 2 hours ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $212 found 3 days ago
Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$216 Roundtrip, found 2 hours ago
$216
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $216 found 2 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $217 just found
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $222 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$222 Roundtrip, just found
$222
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $222 just found
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 5 days ago
$224
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $224 found 5 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $227 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$227 Roundtrip, just found
$227
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $227 just found
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $229 found 3 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $232 found 1 day ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$233 Roundtrip, found 4 days ago
$233
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $233 found 4 days ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$234 Roundtrip, found 5 days ago
$234
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $234 found 5 days ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 2 days ago
$235
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $235 found 2 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$238 Roundtrip, found 4 days ago
$238
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $238 found 4 days ago
Fly Play
Wed, Jul 9 - Wed, Aug 20
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$754 Roundtrip, found 3 days ago
$754
Roundtrip
found 3 days ago
Select Fly Play flight, departing Wed, Jul 9 from Roissy-Charles de Gaulle to Stewart Intl., returning Wed, Aug 20, priced at $754 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 July, 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 $206, 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 $206 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$205

Last Minute Hotel Deals in Middletown

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! (1,005 reviews)
"Friendly staff"

Reviewed on Jun 16, 2025

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Sleep Inn & Suites Middletown - Goshen
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 (1,004 reviews)
"Very Reasonable Very Quiet Very Friendly"

Reviewed on Jun 13, 2025

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Super 8 by Wyndham 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! (718 reviews)
"Very comfortable and employees were very welcoming. The room was large and the bed comfortable."

Reviewed on Jun 16, 2025

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La Quinta Inn & Suites by Wyndham 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! (1,000 reviews)
"Breakfast was a nice option for something simple to get the day going. Staff was nice and it was conveniently located. Room was clean and ready when we got there!"

Reviewed on Jun 16, 2025

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Hampton Inn by Hilton Middletown
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! (905 reviews)
"Nothing else to add"

Reviewed on Jun 13, 2025

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Courtyard by Marriott Middletown Goshen
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)
"Very nice property, room was great. Two minor disappointments: only 1 hanger in the closet, I arrived at 10:30 PM and was tired so I told the front desk at checkout. Breakfast skimpy. No hot breakfast, toast and dry cereal, just and coffee. I will stay here again."

Reviewed on Jun 16, 2025

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Microtel Inn & Suites 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! (690 reviews)
"Fast, efficient,"

Reviewed on Jun 4, 2025

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Home2 Suites by Hilton Middletown
Candlewood Suites Middletown Goshen by IHG
Candlewood Suites Middletown Goshen by IHG
2.5 out of 5
21 Med Parc Road, Middletown, NY
Stay at this hotel in Middletown. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
8/10 Very Good! (6 reviews)
"It was brand new and everyone was very helpful!"

Reviewed on Jun 16, 2025

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Candlewood Suites Middletown Goshen by IHG
See all 1,438 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.