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New Windsor

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New Windsor Flights as Low as $114

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

Allegiant Air
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Sep 6, priced at $114 found 4 days ago
Allegiant Air
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Sep 6, priced at $119 found 2 days ago
Allegiant Air
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Sep 6, priced at $124 found 5 days ago
Allegiant Air
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Sep 6, priced at $130 found 2 days ago
Breeze Airways
Thu, Sep 10 - Sat, Sep 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$151 Roundtrip, found 1 day ago
$151
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Stewart Intl., returning Sat, Sep 12, priced at $151 found 1 day ago
Allegiant Air
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Sep 6, priced at $154 found 1 day ago
Breeze Airways
Sat, Oct 3 - Sat, Oct 3
TPA
Tampa Intl.
SWF
Stewart Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 3 from Tampa Intl. to Stewart Intl., returning Sat, Oct 3, priced at $171 found 1 day ago
Breeze Airways
Fri, Sep 4 - Fri, Sep 11
CHS
Charleston Intl.
SWF
Stewart Intl.
$192 Roundtrip, found 11 hours ago
$192
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Sep 4 from Charleston Intl. to Stewart Intl., returning Fri, Sep 11, priced at $192 found 11 hours ago
American Airlines
Tue, Sep 8 - Tue, Sep 8
MCO
Orlando Intl.
HPN
Westchester County
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 8 from Orlando Intl. to Westchester County, returning Tue, Sep 8, priced at $214 found 2 days ago
Breeze Airways
Sat, Sep 12 - Tue, Sep 29
TPA
Tampa Intl.
HPN
Westchester County
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 12 from Tampa Intl. to Westchester County, returning Tue, Sep 29, priced at $239 found 1 day ago
Allegiant Air
Thu, Sep 3 - Thu, Sep 3
MYR
Myrtle Beach Intl.
SWF
Stewart Intl.
$266 Roundtrip, found 1 day ago
$266
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Sep 3 from Myrtle Beach Intl. to Stewart Intl., returning Thu, Sep 3, priced at $266 found 1 day ago
JetBlue Airways
Thu, Sep 17 - Tue, Sep 29
MCO
Orlando Intl.
HPN
Westchester County
$282 Roundtrip, found 2 hours ago
$282
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Sep 17 from Orlando Intl. to Westchester County, returning Tue, Sep 29, priced at $282 found 2 hours ago
JetBlue Airways
Sat, Oct 3 - Wed, Oct 7
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$287 Roundtrip, found 3 hours ago
$287
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Oct 3 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Wed, Oct 7, priced at $287 found 3 hours ago
Delta
Sat, Oct 3 - Wed, Oct 7
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$307 Roundtrip, found 3 hours ago
$307
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Oct 3 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Wed, Oct 7, priced at $307 found 3 hours ago
JetBlue Airways
Fri, Sep 4 - Fri, Sep 11
RSW
Southwest Florida Intl.
HPN
Westchester County
$317 Roundtrip, found 6 days ago
$317
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, Sep 4 from Southwest Florida Intl. to Westchester County, returning Fri, Sep 11, priced at $317 found 6 days ago
Breeze Airways
Fri, Sep 4 - Mon, Sep 7
RSW
Southwest Florida Intl.
SWF
Stewart Intl.
$415 Roundtrip, found 11 hours ago
$415
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Sep 4 from Southwest Florida Intl. to Stewart Intl., returning Mon, Sep 7, priced at $415 found 11 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 $114, 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 $114 right now, why wait?

New Windsor Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$114

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 ...
8.4/10 Very Good! (1,022 reviews)
"Very skeptical of staying at a Red Roof Inn as I think they have a bad rep, but we were very pleased with this hotel. It was very reasonable, the view was lovely of the river and the rooms were comfortable. Location wasn't great, especially if you don't have a vehicle (which we didn't) but if we ..."

Reviewed on Aug 19, 2026

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 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! (1,003 reviews)
"Great place to stay"

Reviewed on Aug 19, 2026

Get rates
Homewood Suites Stewart Airport
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,044 reviews)
"The room was not ready at 3pm. We had to wait over an hour for a room to be available."

Reviewed on Aug 19, 2026

Get rates
Hyatt Place Poughkeepsie / Hudson Valley
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 ...
Get rates
Sleep Inn & Suites Middletown - Goshen
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. ...
8.8/10 Excellent! (1,011 reviews)
"Bathroom: The placement of the towel rack was confusing No light over the toilet No exhaust fan Pool: We chose this hotel because of the outdoor pool. We called the property to check. Not told the truth. It was obvious the pool/area has been derelict for years."

Reviewed on Aug 18, 2026

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Holiday Inn Express Poughkeepsie by IHG
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! (1,008 reviews)
"It was a pleasure to stay there"

Reviewed on Aug 19, 2026

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La Quinta Inn & Suites by Wyndham Middletown-Goshen
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts ...
4.8/10 (999 reviews)
"It was a slum. Stayed one night, wasn't vacuumed, dirty walls. Was afraid of bed bugs so left lights on and didn't sleep. Highlight was feeding homeless guy outside. Would have let him in hallway but he was safer out there."

Reviewed on Aug 18, 2026

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Ramada by Wyndham Newburgh/West Point
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,009 reviews)
"Super clean and great room!"

Reviewed on Aug 19, 2026

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DoubleTree by Hilton Poughkeepsie Convention Center
See all 1,023 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 ...
8.4/10 Very Good! (1,022 reviews)
"Very skeptical of staying at a Red Roof Inn as I think they have a bad rep, but we were very pleased with this hotel. It was very reasonable, the view was lovely of the river and the rooms were comfortable. Location wasn't great, especially if you don't have a vehicle (which we didn't) but if we ..."

Reviewed on Aug 19, 2026

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 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! (1,003 reviews)
"Great place to stay"

Reviewed on Aug 19, 2026

Get rates
Homewood Suites Stewart Airport
See all 1,023 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.