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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.

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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
$140

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 ...
8.8/10 Excellent! (1,004 reviews)
We checked in late and the gentleman at the front desk was extremely pleasant and helpful. After a long drive, we appreciated his kindness.

Reviewed on Apr 15, 2026

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
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (1,015 reviews)
Breakfast is over at 10am, the pool is open in the evening very small but overall good for kids. Great stay and price.

Reviewed on Apr 15, 2026

Courtyard by Marriott 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
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 ...
9.4/10 Exceptional! (999 reviews)
The place is pleasant; the service is excellent, and the staff are very helpful and attentive. The room was spacious, with comfortable beds and pillows. Our stay at La Quinta was fantastic! Just outside the hotel, we found a variety of restaurants and fast-food options, as well as various attractions, ...

Reviewed on Apr 12, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 ...
8.6/10 Excellent! (998 reviews)
Fresh breakfast each morning

Reviewed on Apr 16, 2026

Tru by Hilton 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 ...
8.6/10 Excellent! (1,000 reviews)
Clean room

Reviewed on Apr 15, 2026

Hampton Inn by Hilton Middletown
Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
20 MED PARC 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 helpful staff and the clean ...
8.8/10 Excellent! (710 reviews)
Plenty of parking. Breakfast OK - more sweet rolls, please.

Reviewed on Apr 13, 2026

Holiday Inn Express & Suites Middletown - Goshen by IHG
Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen

3 out of 5
57 TOWER DRIVE 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 in our reviews. ...
9.4/10 Exceptional! (325 reviews)
Breakfast was cold, but still yummy. Room was clean. Staff was nice.

Reviewed on Apr 13, 2026

Residence Inn by Marriott Middletown Goshen
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

3 out of 5
600 Route 211 East 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 in our reviews. ...
9/10 Wonderful! (762 reviews)
Very central to a lot of places like restaurants and stores. Also place is very clean and nice. Would def stay again

Reviewed on Apr 13, 2026

Home2 Suites by Hilton 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.