Search Cheap Flights to
Middletown

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Middletown Flights as Low as $160

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

Breeze Airways
Fri, Feb 14 - Tue, Feb 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Feb 14 from Orlando Intl. to Stewart Intl., returning Tue, Feb 18, priced at $160 found 4 days ago
Breeze Airways
Thu, Apr 10 - Mon, Apr 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Apr 10 from Orlando Intl. to Stewart Intl., returning Mon, Apr 21, priced at $174 found 1 day ago
Breeze Airways
Tue, Jul 8 - Fri, Jul 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Fri, Jul 11, priced at $206 found 1 day ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$213 Roundtrip, found 2 days ago
$213
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $213 found 2 days ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$213 Roundtrip, found 2 days ago
$213
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $213 found 2 days ago
Breeze Airways
Fri, Feb 7 - Mon, Feb 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$217 Roundtrip, found 15 hours ago
$217
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, Feb 7 from Orlando Intl. to Stewart Intl., returning Mon, Feb 10, priced at $217 found 15 hours ago
Breeze Airways
Thu, Jun 26 - Mon, Jun 30
MCO
Orlando Intl.
SWF
Stewart Intl.
$228 Roundtrip, found 18 hours ago
$228
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Mon, Jun 30, priced at $228 found 18 hours ago
Breeze Airways
Sun, Apr 13 - Mon, Apr 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Apr 13 from Orlando Intl. to Stewart Intl., returning Mon, Apr 21, priced at $238 found 1 day ago
Breeze Airways
Thu, Feb 13 - Sun, Feb 16
MCO
Orlando Intl.
SWF
Stewart Intl.
$239 Roundtrip, found 4 days ago
$239
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Feb 13 from Orlando Intl. to Stewart Intl., returning Sun, Feb 16, priced at $239 found 4 days ago
Breeze Airways
Fri, Apr 25 - Sun, Apr 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$249 Roundtrip, found 5 days ago
$249
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Orlando Intl. to Stewart Intl., returning Sun, Apr 27, priced at $249 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Orlando Intl. to Stewart Intl., returning Mon, Apr 28, priced at $257 found 5 days ago
Breeze Airways
Fri, Aug 8 - Mon, Aug 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 8 from Orlando Intl. to Stewart Intl., returning Mon, Aug 11, priced at $257 found 1 day ago
Breeze Airways
Fri, Feb 7 - Mon, Feb 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$261 Roundtrip, found 5 days ago
$261
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Feb 7 from Orlando Intl. to Stewart Intl., returning Mon, Feb 10, priced at $261 found 5 days ago
Breeze Airways
Tue, Jul 8 - Sun, Jul 13
MCO
Orlando Intl.
SWF
Stewart Intl.
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Sun, Jul 13, priced at $264 found 1 day ago
Breeze Airways
Tue, Jul 15 - Fri, Jul 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 15 from Orlando Intl. to Stewart Intl., returning Fri, Jul 18, priced at $269 found 1 day ago
Fly Play
Thu, Aug 21 - Sun, Aug 31
STN
Stansted
SWF
Stewart Intl.
$755 Roundtrip, found 16 hours ago
$755
Roundtrip
found 16 hours ago
Select Fly Play flight, departing Thu, Aug 21 from Stansted to Stewart Intl., returning Sun, Aug 31, priced at $755 found 16 hours 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 February, 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 $160, 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 $160 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$159

Last Minute Hotel Deals in Middletown

Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
The price is $106 per night from Feb 6 to Feb 7
$106
includes taxes & fees
Feb 6 - Feb 7
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! (827 reviews)
"Overall great service"

Reviewed on Jan 26, 2025

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
The price is $99 per night from Feb 13 to Feb 14
$99
includes taxes & fees
Feb 13 - Feb 14
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! (1,001 reviews)
"I was a little afraid of the bath tub as it was slippery with no mat. Otherwise all was well."

Reviewed on Jan 27, 2025

Hampton Inn by Hilton Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
The price is $96 per night from Feb 16 to Feb 17
$96
includes taxes & fees
Feb 16 - Feb 17
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 ...
8.6/10 Excellent! (1,003 reviews)
"Everything was fine, except i had trouble with the thermostat & raising the temperature in my room."

Reviewed on Jan 21, 2025

Sleep Inn & Suites Middletown - Goshen
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 out of 5
41 Dunning Road, Middletown, NY
The price is $99 per night from Feb 9 to Feb 10
$99
includes taxes & fees
Feb 9 - Feb 10
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! (844 reviews)
"Super friendly staff, great amenities for a reasonable cost."

Reviewed on Jan 29, 2025

Tru by Hilton Middletown
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
The price is $110 per night from Feb 16 to Feb 17
$110
includes taxes & fees
Feb 16 - Feb 17
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 ...
9.2/10 Wonderful! (620 reviews)
You should stay here
"I always enjoy my stay here and I do stay often. I give five stars because even if I’ve ever had an issue it’s immediately resolved. I try not to bother the staff too much and they are always asking me do I need anything because of that. They are very attentive. Whenever they see me they are kind ..."

Reviewed on Jan 24, 2025

La Quinta 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
The price is $133 per night from Feb 9 to Feb 10
$133
includes taxes & fees
Feb 9 - Feb 10
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. ...
9/10 Wonderful! (652 reviews)
"Nice and clean, easy to check in and room is nice."

Reviewed on Feb 1, 2025

Home2 Suites by Hilton Middletown
Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
2.5 out of 5
20 MED PARC ROAD, Middletown, NY
The price is $122 per night from Feb 9 to Feb 10
$122
includes taxes & fees
Feb 9 - Feb 10
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 ...
8.6/10 Excellent! (646 reviews)
"Very nice hotel with friendly staff."

Reviewed on Jan 31, 2025

Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel
Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown Goshen
3 out of 5
57 TOWER DRIVE, Middletown, NY
The price is $169 per night from Feb 16 to Feb 17
$169
includes taxes & fees
Feb 16 - Feb 17
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. ...
9.4/10 Exceptional! (275 reviews)
"Excellent"

Reviewed on Feb 2, 2025

Residence Inn by Marriott Middletown Goshen
See all 1,390 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.