Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $164

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

Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 4 days ago
$164
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $164 found 4 days ago
Breeze Airways
Mon, Aug 11 - Tue, Aug 12
MCO
Orlando Intl.
HPN
Westchester County
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Aug 11 from Orlando Intl. to Westchester County, returning Tue, Aug 12, priced at $167 found 4 days ago
Breeze Airways
Thu, Oct 9 - Mon, Oct 13
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 16 hours ago
$169
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Thu, Oct 9 from Orlando Intl. to Stewart Intl., returning Mon, Oct 13, priced at $169 found 16 hours ago
Breeze Airways
Mon, Aug 11 - Tue, Aug 12
MCO
Orlando Intl.
HPN
Westchester County
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Aug 11 from Orlando Intl. to Westchester County, returning Tue, Aug 12, priced at $172 found 4 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $173 found 6 days ago
JetBlue Airways
Tue, Aug 12 - Mon, Aug 18
MCO
Orlando Intl.
HPN
Westchester County
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Aug 12 from Orlando Intl. to Westchester County, returning Mon, Aug 18, priced at $175 found 4 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $176 found 6 days ago
Breeze Airways
Mon, Aug 18 - Fri, Aug 22
GSP
Greenville-Spartanburg Intl.
HPN
Westchester County
$178 Roundtrip, found 16 hours ago
$178
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 18 from Greenville-Spartanburg Intl. to Westchester County, returning Fri, Aug 22, priced at $178 found 16 hours ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $178 found 6 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$179 Roundtrip, found 23 hours ago
$179
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $179 found 23 hours ago
Breeze Airways
Mon, Aug 18 - Fri, Aug 22
GSP
Greenville-Spartanburg Intl.
HPN
Westchester County
$183 Roundtrip, found 16 hours ago
$183
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 18 from Greenville-Spartanburg Intl. to Westchester County, returning Fri, Aug 22, priced at $183 found 16 hours ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $183 found 6 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $189 found 1 day ago
Delta
Sun, Aug 10 - Wed, Aug 20
MCO
Orlando Intl.
HPN
Westchester County
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Aug 10 from Orlando Intl. to Westchester County, returning Wed, Aug 20, priced at $206 found 4 days ago
American Airlines
Mon, Aug 11 - Tue, Aug 12
MCO
Orlando Intl.
HPN
Westchester County
$211 Roundtrip, found 4 days ago
$211
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Aug 11 from Orlando Intl. to Westchester County, returning Tue, Aug 12, priced at $211 found 4 days ago
Breeze Airways
Fri, Aug 15 - Sun, Aug 24
GSP
Greenville-Spartanburg Intl.
SWF
Stewart Intl.
$579 Roundtrip, found 16 hours ago
$579
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Greenville-Spartanburg Intl. to Stewart Intl., returning Sun, Aug 24, priced at $579 found 16 hours ago

Cheap Flights to New Windsor

Fall in love at first flight with your vacation to New Windsor 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 New Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in New Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to New Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to New Windsor 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 NYC airport.

What is the cheapest month to fly to New Windsor?

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 New Windsor are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to New Windsor?

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 New Windsor.

What airport is best to fly into New Windsor?

When you’re planning your trip to New Windsor, convenience is the name of the game. Luckily, New Windsor Stewart Intl. Airport is nearby so you can deplane and get going on checking off everything on your New Windsor must-do list.

How much are flights to New Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to New Windsor 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 New Windsor?

The trick to saving a stack of cash on your flight to New Windsor? 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?

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

Last Minute Hotel Deals in New Windsor

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave, New Windsor, NY
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,010 reviews)
Lovely 2 day stay
"The room was clean, the beds were super comfortable. Check in was easy."

Reviewed on Jul 27, 2025

Get rates
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Stay at this 3-star hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (1,000 reviews)
"Buen desayuno. Habitacion limpia y comoda."

Reviewed on Jul 25, 2025

Get rates
Homewood Suites Stewart Airport
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! (771 reviews)
"Place was great have stayed here many times."

Reviewed on Jul 30, 2025

Get rates
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,011 reviews)
"It’s very beautiful place.Gift shop it was amazing.My wife loved it and we bought bunch of gifts."

Reviewed on Jul 27, 2025

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Overlook Lodge at Bear Mountain
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! (1,009 reviews)
Rssb
"The staff was super friendly and the place was nice and clean. Comfortable bed and updated bathroom."

Reviewed on Jul 30, 2025

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Sleep Inn & Suites Middletown - Goshen
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr, Central Valley, NY
Book a stay at this business-friendly hotel in Woodbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,002 reviews)
"Customer service was terrible, not understanding and friendly at all. Other than that hotel was ok but will not stay again due to lack of customer service where people just don't know how to speak to their guest."

Reviewed on Jul 30, 2025

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Hampton Inn Harriman Woodbury
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on Aug 1, 2025

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Holiday Inn Express Poughkeepsie by IHG
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (383 reviews)
"Not bad. Staff was fine."

Reviewed on Jul 30, 2025

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Quality Inn Poughkeepsie
See all 992 properties in New Windsor
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.

Top Hotels With Free Airport Shuttle

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave, New Windsor, NY
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,010 reviews)
Lovely 2 day stay
"The room was clean, the beds were super comfortable. Check in was easy."

Reviewed on Jul 27, 2025

Get rates
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Stay at this 3-star hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (1,000 reviews)
"Buen desayuno. Habitacion limpia y comoda."

Reviewed on Jul 25, 2025

Get rates
Homewood Suites Stewart Airport
See all 992 properties in New Windsor
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.