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New Windsor

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New Windsor Flights as Low as $124

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

Allegiant Air
Thu, Jan 21 - Sun, Jan 24
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$124 Roundtrip, found 17 hours ago
$124
Roundtrip
found 17 hours ago
Select Allegiant Air flight, departing Thu, Jan 21 from St. Petersburg-Clearwater Intl. to Stewart Intl., returning Sun, Jan 24, priced at $124 found 17 hours ago
Breeze Airways
Tue, Jan 26 - Wed, Feb 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Tue, Jan 26 from Raleigh - Durham Intl. to Westchester County, returning Wed, Feb 17, priced at $132 found 5 hours ago
Allegiant Air
Thu, Jan 21 - Sun, Jan 24
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from St. Petersburg-Clearwater Intl. to Stewart Intl., returning Sun, Jan 24, priced at $132 found 3 days ago
Breeze Airways
Tue, Jan 26 - Wed, Feb 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Tue, Jan 26 from Raleigh - Durham Intl. to Westchester County, returning Wed, Feb 17, priced at $137 found 5 hours ago
Breeze Airways
Wed, Dec 2 - Sat, Dec 12
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Dec 2 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Dec 12, priced at $137 found 3 hours ago
Breeze Airways
Sat, Dec 5 - Sat, Dec 12
TPA
Tampa Intl.
SWF
Stewart Intl.
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Tampa Intl. to Stewart Intl., returning Sat, Dec 12, priced at $151 found 3 days ago
Breeze Airways
Fri, Jan 29 - Mon, Feb 1
MCO
Orlando Intl.
SWF
Stewart Intl.
$151 Roundtrip, found 4 days ago
$151
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jan 29 from Orlando Intl. to Stewart Intl., returning Mon, Feb 1, priced at $151 found 4 days ago
Allegiant Air
Thu, Dec 3 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Dec 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Dec 6, priced at $153 found 6 days ago
Breeze Airways
Fri, Jan 22 - Mon, Jan 25
TPA
Tampa Intl.
HPN
Westchester County
$208 Roundtrip, just found
$208
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Jan 22 from Tampa Intl. to Westchester County, returning Mon, Jan 25, priced at $208 just found
Delta
Tue, Jan 26 - Wed, Feb 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$281 Roundtrip, found 5 hours ago
$281
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Jan 26 from Raleigh - Durham Intl. to Westchester County, returning Wed, Feb 17, priced at $281 found 5 hours ago
Breeze Airways
Thu, Nov 26 - Tue, Dec 1
MCO
Orlando Intl.
HPN
Westchester County
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 26 from Orlando Intl. to Westchester County, returning Tue, Dec 1, priced at $308 found 1 day ago
Delta
Sat, Dec 5 - Wed, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$320 Roundtrip, just found
$320
Roundtrip
just found
Select Delta flight, departing Sat, Dec 5 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Wed, Dec 9, priced at $320 just found
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$333 Roundtrip, found 1 hour ago
$333
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Tue, Dec 8, priced at $333 found 1 hour ago
American Airlines
Tue, Jan 26 - Wed, Feb 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$371 Roundtrip, found 5 hours ago
$371
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Jan 26 from Raleigh - Durham Intl. to Westchester County, returning Wed, Feb 17, priced at $371 found 5 hours ago
Delta
Sat, Jan 16 - Wed, Jan 27
LAX
Los Angeles Intl.
HPN
Westchester County
$391 Roundtrip, found 21 hours ago
$391
Roundtrip
found 21 hours ago
Select Delta flight, departing Sat, Jan 16 from Los Angeles Intl. to Westchester County, returning Wed, Jan 27, priced at $391 found 21 hours ago
Delta
Wed, Feb 17 - Mon, Feb 22
ORD
O'Hare Intl.
HPN
Westchester County
$497 Roundtrip, found 19 hours ago
$497
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Feb 17 from O'Hare Intl. to Westchester County, returning Mon, Feb 22, priced at $497 found 19 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 January, 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 $124, 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 $124 right now, why wait?

New Windsor Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$124

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 ...
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! (1,000 reviews)
"Great breakfast selection, very clean property overall"

Reviewed on Nov 3, 2026

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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! (1,171 reviews)
"We had a great time celebrating my wife’s birthday! One bad experience was the next door neighbor, who was awful, very loud and rude in the early am. But other than that no complaints."

Reviewed on Nov 15, 2026

Get rates
Hyatt Place Poughkeepsie / Hudson Valley
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive 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 ...
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Overlook Lodge at Bear Mountain
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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Comfort Suites Fishkill near Interstate 84
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 ...
Get rates
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 ...
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Quality Inn Poughkeepsie
Inn on the Hudson

Inn on the Hudson

2 out of 5
634 Main Street Peekskill NY
Book a stay at this business-friendly hotel in Peekskill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,008 reviews)
"There room was very small. The ceiling over our head in bed was peeling. We asked for an extra pillow and we had to wait until the next morning to get it and the breakfast was practically nonexistent. The only positive i can say was the view of the Hudson. I would definitely not stay there again. ..."

Reviewed on Nov 15, 2026

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Inn on the Hudson
See all 1,053 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 ...
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! (1,000 reviews)
"Great breakfast selection, very clean property overall"

Reviewed on Nov 3, 2026

Get rates
Homewood Suites Stewart Airport
See all 1,053 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.