Search Cheap Flights to
Middletown

Photo by Vincent Ramundo

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Middletown Flights as Low as $119

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

Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$119 Roundtrip, found 19 hours ago
$119
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $119 found 19 hours ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$130 Roundtrip, found 19 hours ago
$130
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $130 found 19 hours ago
Breeze Airways
Tue, Aug 26 - Thu, Aug 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 26 from Orlando Intl. to Stewart Intl., returning Thu, Aug 28, priced at $152 found 3 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $158 found 1 day ago
Breeze Airways
Tue, Aug 26 - Thu, Aug 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 26 from Orlando Intl. to Stewart Intl., returning Thu, Aug 28, priced at $162 found 3 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $164 found 1 day ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 3 hours ago
$164
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $164 found 3 hours ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $169 found 1 day ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 3 hours ago
$169
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $169 found 3 hours ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 3 hours ago
$174
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $174 found 3 hours ago
Breeze Airways
Tue, Aug 19 - Thu, Aug 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 8 hours ago
$180
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Tue, Aug 19 from Orlando Intl. to Stewart Intl., returning Thu, Aug 21, priced at $180 found 8 hours ago
Breeze Airways
Tue, Aug 12 - Thu, Aug 14
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 9 hours ago
$190
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Tue, Aug 12 from Orlando Intl. to Stewart Intl., returning Thu, Aug 14, priced at $190 found 9 hours ago
Breeze Airways
Tue, Aug 12 - Thu, Aug 14
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 9 hours ago
$195
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Tue, Aug 12 from Orlando Intl. to Stewart Intl., returning Thu, Aug 14, priced at $195 found 9 hours ago
Breeze Airways
Tue, Aug 12 - Thu, Aug 14
MCO
Orlando Intl.
SWF
Stewart Intl.
$200 Roundtrip, found 9 hours ago
$200
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Tue, Aug 12 from Orlando Intl. to Stewart Intl., returning Thu, Aug 14, priced at $200 found 9 hours ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$205 Roundtrip, found 3 days ago
$205
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Orlando Intl. to Stewart Intl., returning Sun, Aug 17, priced at $205 found 3 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $209 found 5 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 September, 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 $119, 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 $119 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$118

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! (1,003 reviews)
"While the elevator is always broken and the carpet needs to be replaced in the hallway, my family and I enjoy our stays here. The staff is always pleasant and someone always brews the best iced lemonade tea accessible in the lobby. I look forward to having a cup when I check in."

Reviewed on Aug 6, 2025

Get rates
Sleep Inn & Suites Middletown - Goshen
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! (776 reviews)
"Place was great have stayed here many times."

Reviewed on Jul 30, 2025

Get rates
La Quinta Inn & Suites by Wyndham 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! (942 reviews)
"Clean, quiet and convenient hotel."

Reviewed on Aug 7, 2025

Get rates
Courtyard by Marriott 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 WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.2/10 (1,009 reviews)
"The desk person on check in was fabulous. She really made a friend with my 10 yr old. She was super helpful and friendly. My only complaint was the shower curtain rod wasn't properly anchored. Had no effect on shower though. The 10 yr old loved the pattern on the bedspread."

Reviewed on Aug 2, 2025

Get rates
Super 8 by Wyndham Middletown
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)
"Excellent for a family get away to Legoland."

Reviewed on Aug 4, 2025

Get rates
Hampton Inn 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)
"Workers are very friendly, clean space"

Reviewed on Jul 31, 2025

Get rates
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! (706 reviews)
"The room is very spacious and clean. It comes with kitchen utensils, plates, glasses, and extra movable table to use as a dining table!!"

Reviewed on Aug 1, 2025

Get rates
Home2 Suites by Hilton 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! (305 reviews)
"Very helpful staff"

Reviewed on Aug 2, 2025

Get rates
Residence Inn by Marriott Middletown Goshen
See all 1,418 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.