Search Cheap Flights to
Middletown

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Middletown Flights as Low as $164

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

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
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
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 $169 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 2 days ago
$174
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 $174 found 2 days ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $181 found 15 hours ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$191 Roundtrip, found 15 hours ago
$191
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $191 found 15 hours ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $195 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $200 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$205 Roundtrip, found 2 days ago
$205
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $205 found 2 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $225 found 4 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $230 found 4 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$231 Roundtrip, found 3 days ago
$231
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $231 found 3 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $235 found 4 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $240 found 4 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$241 Roundtrip, found 3 days ago
$241
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $241 found 3 days ago
Breeze Airways
Thu, May 22 - Mon, May 26
MCO
Orlando Intl.
SWF
Stewart Intl.
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 22 from Orlando Intl. to Stewart Intl., returning Mon, May 26, priced at $245 found 4 days ago
Breeze Airways
Thu, Jun 12 - Mon, Jun 16
MCO
Orlando Intl.
SWF
Stewart Intl.
$251 Roundtrip, found 4 days ago
$251
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 12 from Orlando Intl. to Stewart Intl., returning Mon, Jun 16, priced at $251 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 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 $164, 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 $164 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$163

Last Minute Hotel Deals in 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 $150 per night from May 6 to May 7
$150
includes taxes & fees
May 6 - May 7
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! (687 reviews)
"The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again."

Reviewed on Apr 29, 2025

La Quinta Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
The price is $134 per night from May 26 to May 27
$134
includes taxes & fees
May 26 - May 27
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! (1,000 reviews)
"Great property close to legoland. We saw some ants coming out from an outlet into our room on the second day. We quickly made sure to put our food items in the fridge."

Reviewed on Apr 28, 2025

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
The price is $130 per night from May 26 to May 27
$130
includes taxes & fees
May 26 - May 27
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! (875 reviews)
"The room was not cleaned between our 2 night stay"

Reviewed on Apr 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 $132 per night from May 26 to May 27
$132
includes taxes & fees
May 26 - May 27
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)
"Good location except not much choice for food. Only Outback nearby."

Reviewed on Apr 27, 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 $173 per night from May 26 to May 27
$173
includes taxes & fees
May 26 - May 27
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! (673 reviews)
Great place to stay
"Great place to stay. Great service. Room was clean. Only negative was the pool was could’ve been cleaner. Water was cloudy. Other then that we had a great time and it was very close to LEGOLAND."

Reviewed on Apr 18, 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 $89 per night from May 8 to May 9
$89
includes taxes & fees
May 8 - May 9
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 (1,001 reviews)
"It was in walking distance to places that I’ve shopped and done business with on a regular basis"

Reviewed on Apr 25, 2025

Super 8 by Wyndham Middletown
Tru by Hilton Middletown
Tru by Hilton Middletown
2.5 out of 5
41 Dunning Road, 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! (910 reviews)
"Perfect stay for a quick trip."

Reviewed on Apr 28, 2025

Get rates
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 $223 per night from May 11 to May 12
$223
includes taxes & fees
May 11 - May 12
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! (291 reviews)
"All round excellent"

Reviewed on Apr 1, 2025

Residence Inn by Marriott Middletown Goshen
See all 1,404 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.