Search Cheap Flights to
Middletown

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Middletown Flights as Low as $140

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

Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $140 found 2 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$143 Roundtrip, found 18 hours ago
$143
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $143 found 18 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $145 found 2 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$146 Roundtrip, found 18 hours ago
$146
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $146 found 18 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $150 found 2 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$153 Roundtrip, found 18 hours ago
$153
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $153 found 18 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $155 found 2 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$157 Roundtrip, found 18 hours ago
$157
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $157 found 18 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $157 found 6 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $160 found 2 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$162 Roundtrip, found 6 hours ago
$162
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $162 found 6 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$165 Roundtrip, found 2 days ago
$165
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $165 found 2 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$168 Roundtrip, found 6 hours ago
$168
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $168 found 6 hours ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $188 found 4 days ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $193 found 4 days ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $198 found 4 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 May, 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 $140, 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 $140 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$139

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
The price is $152 per night from Apr 28 to Apr 29
$152
includes taxes & fees
Apr 28 - Apr 29
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, clean, and updated rooms"

Reviewed on Apr 10, 2025

Sleep Inn & Suites Middletown - Goshen
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 $157 per night from Apr 29 to Apr 30
$157
includes taxes & fees
Apr 29 - Apr 30
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! (667 reviews)
"Really nice hotel with great staff. The rooms was really clean."

Reviewed on Apr 6, 2025

La Quinta Inn & Suites by Wyndham Middletown
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
The price is $119 per night from Apr 27 to Apr 28
$119
includes taxes & fees
Apr 27 - Apr 28
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! (856 reviews)
"This is the only hotel we have stayed out in ten years that didn’t offer complimentary coffee in the lobby."

Reviewed on Apr 9, 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 $135 per night from May 4 to May 5
$135
includes taxes & fees
May 4 - May 5
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! (1,000 reviews)
"Good location"

Reviewed on Mar 30, 2025

Hampton Inn by Hilton Middletown
Home2 Suites by Hilton Middletown
Home2 Suites by Hilton Middletown
3 out of 5
600 Route 211 East, Middletown, NY
The price is $163 per night from Apr 30 to May 1
$163
includes taxes & fees
Apr 30 - May 1
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! (669 reviews)
"Overnight stay. Overall great service"

Reviewed on Mar 23, 2025

Home2 Suites 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
The price is $84 per night from Apr 20 to Apr 21
$84
includes taxes & fees
Apr 20 - Apr 21
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 (1,002 reviews)
"Well situated for our needs"

Reviewed on Apr 6, 2025

Super 8 by Wyndham Middletown
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 out of 5
41 Dunning Road, Middletown, NY
The price is $150 per night from Apr 20 to Apr 21
$150
includes taxes & fees
Apr 20 - Apr 21
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! (902 reviews)
"Very good check in and out, good stay, will be back next time."

Reviewed on Mar 31, 2025

Tru by Hilton Middletown
Residence Inn by Marriott Middletown Goshen
Residence Inn by Marriott Middletown Goshen
3 out of 5
57 TOWER DRIVE, Middletown, NY
The price is $190 per night from Apr 27 to Apr 28
$190
includes taxes & fees
Apr 27 - Apr 28
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! (290 reviews)
"All round excellent"

Reviewed on Apr 1, 2025

Residence Inn by Marriott Middletown Goshen
See all 1,402 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.