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Middletown

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Middletown Flights as Low as $180

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

Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $180 found 6 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $183 found 6 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$185 Roundtrip, found 6 days ago
$185
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $185 found 6 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $190 found 6 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$194 Roundtrip, found 6 days ago
$194
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $194 found 6 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $201 found 6 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $206 found 4 days ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $217 found 6 days ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $219 found 1 day ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $222 found 6 days ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $224 found 1 day ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$227 Roundtrip, found 6 days ago
$227
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $227 found 6 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $228 found 2 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$229 Roundtrip, found 2 days ago
$229
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $229 found 2 days ago
Breeze Airways
Wed, Aug 19 - Sat, Aug 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$234 Roundtrip, found 3 days ago
$234
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Stewart Intl., returning Sat, Aug 22, priced at $234 found 3 days ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 2 days ago
$235
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $235 found 2 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 $180, 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 $180 right now, why wait?

Middletown Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$179

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! (1,028 reviews)
"Hotel was really nice, so clean and breakfast was great! Coffee bar was excellent! Only complaint would be the hotel let people rent out the pool and my family & our guests who stayed at the hotel with us weren’t able to use the pool. Plus it was quite wild in there so it was not appropriate for ..."

Reviewed on Jun 4, 2026

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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
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! (1,010 reviews)
"One of the best La Quinta’s I have been to . Perfect area , lovely staff , clean room . Wish I stayed longer"

Reviewed on Jun 8, 2026

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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! (1,005 reviews)
"Hotel and staff were excellent. Hotel was a bit stark outside (lacked any welcoming landscaping, no flowers or shrubs) but it’s all about the stay inside. Staff was professional and polite, lobby clean but odd furniture. Weird high sided couches. Again, all about the room. Room was on third floor, ..."

Reviewed on May 28, 2026

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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! (1,008 reviews)
"It was a pleasant and comfortable one night stay for us. Everything was as advertised with nice breakfast, supportive staff, and friendly ambience."

Reviewed on Jun 7, 2026

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Hampton Inn by Hilton Middletown
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 ...
8.4/10 Very Good! (1,003 reviews)
"The room was clean but staff was not as friendly as expected for a hotel they didn’t even greet you unless you greeted them first."

Reviewed on May 22, 2026

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Courtyard by Marriott Middletown Goshen
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
563 Route 211 E 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 ...
6/10 (1,002 reviews)
"Promised breakfast...1 pop tarts and a little container of juice. Staff is awesome and well run. Room clean and adequate. I enjoyed my stay here for many days. Quiet. Close to many stores and restaurants. Everyone was so courteous and helpful"

Reviewed on Jun 7, 2026

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Super 8 by Wyndham 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! (726 reviews)
"Great wheelchair accessible bathrooms, big enough to move around and transfer from chair. Staff very friendly. Gave us a late check out as we were racing that mourning. Close by resturants good choice."

Reviewed on Jun 8, 2026

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Holiday Inn Express & Suites Middletown - Goshen by IHG
Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG

2.5 out of 5
21 Med Parc Road Middletown NY
Stay at this hotel in Middletown. Enjoy a 24-hour fitness center, a 24-hour front desk, and conference space. Popular attractions LEGOLAND® New York and Galleria ...
9.2/10 Wonderful! (59 reviews)
"Very friendly staff. Room was spacious and clean. Will return again!"

Reviewed on May 29, 2026

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Candlewood Suites Middletown Goshen by IHG
See all 1,516 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.