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New Windsor

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New Windsor Flights as Low as $127

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

Breeze Airways
Wed, Oct 28 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Oct 28 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at $127 found 2 days ago
Breeze Airways
Wed, Oct 28 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Oct 28 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at $132 found 2 days ago
Breeze Airways
Thu, Nov 26 - Tue, Dec 1
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$132 Roundtrip, found 20 hours ago
$132
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Westchester County, returning Tue, Dec 1, priced at $132 found 20 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Oct 28 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at $137 found 2 days ago
Breeze Airways
Thu, Sep 24 - Sat, Sep 26
MCO
Orlando Intl.
SWF
Stewart Intl.
$166 Roundtrip, just found
$166
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Sep 24 from Orlando Intl. to Stewart Intl., returning Sat, Sep 26, priced at $166 just found
Breeze Airways
Thu, Oct 29 - Tue, Nov 17
MYR
Myrtle Beach Intl.
HPN
Westchester County
$191 Roundtrip, found 14 hours ago
$191
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Myrtle Beach Intl. to Westchester County, returning Tue, Nov 17, priced at $191 found 14 hours ago
Allegiant Air
Fri, Sep 25 - Mon, Sep 28
MYR
Myrtle Beach Intl.
SWF
Stewart Intl.
$216 Roundtrip, found 6 days ago
$216
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Sep 25 from Myrtle Beach Intl. to Stewart Intl., returning Mon, Sep 28, priced at $216 found 6 days ago
Breeze Airways
Wed, Oct 7 - Tue, Oct 13
MCO
Orlando Intl.
HPN
Westchester County
$222 Roundtrip, just found
$222
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Oct 7 from Orlando Intl. to Westchester County, returning Tue, Oct 13, priced at $222 just found
American Airlines
Tue, Mar 2 - Tue, Mar 9
JAX
Jacksonville Intl.
HPN
Westchester County
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 2 from Jacksonville Intl. to Westchester County, returning Tue, Mar 9, priced at $239 found 1 day ago
Delta
Tue, Oct 13 - Sat, Oct 17
JAX
Jacksonville Intl.
HPN
Westchester County
$242 Roundtrip, just found
$242
Roundtrip
just found
Select Delta flight, departing Tue, Oct 13 from Jacksonville Intl. to Westchester County, returning Sat, Oct 17, priced at $242 just found
JetBlue Airways
Wed, Oct 7 - Tue, Oct 13
MCO
Orlando Intl.
HPN
Westchester County
$281 Roundtrip, just found
$281
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Oct 7 from Orlando Intl. to Westchester County, returning Tue, Oct 13, priced at $281 just found
American Airlines
Wed, Nov 18 - Tue, Dec 1
SAN
San Diego Intl.
HPN
Westchester County
$341 Roundtrip, found 17 hours ago
$341
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Nov 18 from San Diego Intl. to Westchester County, returning Tue, Dec 1, priced at $341 found 17 hours ago
American Airlines
Sun, Sep 27 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$413 Roundtrip, found 3 days ago
$413
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Sep 27 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Mon, Oct 5, priced at $413 found 3 days ago
American Airlines
Mon, Nov 23 - Tue, Dec 1
CLT
Charlotte-Douglas Intl.
HPN
Westchester County
$455 Roundtrip, found 17 hours ago
$455
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Mon, Nov 23 from Charlotte-Douglas Intl. to Westchester County, returning Tue, Dec 1, priced at $455 found 17 hours ago
Alaska Airlines
Wed, Nov 18 - Tue, Dec 1
SAN
San Diego Intl.
HPN
Westchester County
$613 Roundtrip, found 17 hours ago
$613
Roundtrip
found 17 hours ago
Select Alaska Airlines flight, departing Wed, Nov 18 from San Diego Intl. to Westchester County, returning Tue, Dec 1, priced at $613 found 17 hours ago
American Airlines
Sat, Nov 21 - Sat, Nov 28
CLD
McClellan-Palomar
HPN
Westchester County
$1,030 Roundtrip, found 17 hours ago
$1,030
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Nov 21 from McClellan-Palomar to Westchester County, returning Sat, Nov 28, priced at $1,030 found 17 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 October, 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 $127, 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 $127 right now, why wait?

New Windsor Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$126

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! (1,015 reviews)
"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."

Reviewed on Sep 8, 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! (1,000 reviews)
"Great place to stay"

Reviewed on Aug 19, 2026

Get rates
Homewood Suites Stewart Airport
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
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 ...
8.4/10 Very Good! (1,000 reviews)
"Quedamos encantados con nuestra visita, esperamos volver."

Reviewed on Sep 9, 2026

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Overlook Lodge at Bear Mountain
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! (1,001 reviews)
"Good location, but the room needs repair; the bathtub and sink retain water."

Reviewed on Sep 9, 2026

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Holiday Inn Express Poughkeepsie by IHG
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! (1,070 reviews)
"I love coming here! It is the best experience ever!"

Reviewed on Sep 9, 2026

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Hyatt Place Poughkeepsie / Hudson Valley
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3 out of 5
1 LEGOLAND BLVD Goshen NY
Book a stay at this family-friendly hotel in Goshen. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions LEGOLAND® New York and Triangle ...
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LEGOLAND Hotel NEW York
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery ...
Get rates
Wildflower Farms, Auberge Collection
See all 1,052 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! (1,015 reviews)
"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."

Reviewed on Sep 8, 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! (1,000 reviews)
"Great place to stay"

Reviewed on Aug 19, 2026

Get rates
Homewood Suites Stewart Airport
See all 1,052 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.