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New Windsor

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New Windsor Flights as Low as $113

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

Breeze Airways
Wed, Mar 11 - Mon, Mar 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Mar 11 from Raleigh - Durham Intl. to Westchester County, returning Mon, Mar 16, priced at $113 found 1 day ago
Breeze Airways
Wed, Mar 18 - Mon, Mar 23
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Mar 18 from Raleigh - Durham Intl. to Westchester County, returning Mon, Mar 23, priced at $117 found 4 days ago
Breeze Airways
Wed, Mar 11 - Mon, Mar 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Mar 11 from Raleigh - Durham Intl. to Westchester County, returning Mon, Mar 16, priced at $118 found 1 day ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $122 found 1 day ago
Breeze Airways
Wed, Mar 11 - Mon, Mar 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Mar 11 from Raleigh - Durham Intl. to Westchester County, returning Mon, Mar 16, priced at $123 found 1 day ago
Breeze Airways
Wed, Mar 18 - Mon, Mar 23
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Mar 18 from Raleigh - Durham Intl. to Westchester County, returning Mon, Mar 23, priced at $127 found 4 days ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $132 found 1 day ago
Breeze Airways
Fri, Jan 30 - Mon, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$133 Roundtrip, found 6 days ago
$133
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 2, priced at $133 found 6 days ago
American Airlines
Thu, Feb 19 - Mon, Feb 23
MCO
Orlando Intl.
HPN
Westchester County
$145 Roundtrip, found 7 hours ago
$145
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Feb 19 from Orlando Intl. to Westchester County, returning Mon, Feb 23, priced at $145 found 7 hours ago
JetBlue Airways
Fri, Feb 6 - Tue, Feb 10
TPA
Tampa Intl.
HPN
Westchester County
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Feb 6 from Tampa Intl. to Westchester County, returning Tue, Feb 10, priced at $152 found 2 days ago
American Airlines
Fri, Feb 6 - Tue, Feb 10
TPA
Tampa Intl.
HPN
Westchester County
$161 Roundtrip, found 2 days ago
$161
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Feb 6 from Tampa Intl. to Westchester County, returning Tue, Feb 10, priced at $161 found 2 days ago
Delta
Wed, Mar 18 - Wed, Mar 25
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Mar 18 from Raleigh - Durham Intl. to Westchester County, returning Wed, Mar 25, priced at $177 found 6 days ago
JetBlue Airways
Thu, Apr 23 - Mon, Apr 27
MCO
Orlando Intl.
HPN
Westchester County
$187 Roundtrip, just found
$187
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Apr 23 from Orlando Intl. to Westchester County, returning Mon, Apr 27, priced at $187 just found
JetBlue Airways
Fri, Feb 13 - Mon, Feb 16
RSW
Southwest Florida Intl.
HPN
Westchester County
$192 Roundtrip, found 18 hours ago
$192
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Fri, Feb 13 from Southwest Florida Intl. to Westchester County, returning Mon, Feb 16, priced at $192 found 18 hours ago
American Airlines
Mon, Feb 23 - Mon, Mar 9
IAH
George Bush Intercontinental
HPN
Westchester County
$257 Roundtrip, found 18 hours ago
$257
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Mon, Feb 23 from George Bush Intercontinental to Westchester County, returning Mon, Mar 9, priced at $257 found 18 hours ago
Accessrail
Sat, Jan 31 - Tue, Feb 3
AVT
Aventura Brightline Train Station
HPN
Westchester County
$503 Roundtrip, found 18 hours ago
$503
Roundtrip
found 18 hours ago
Select Accessrail flight, departing Sat, Jan 31 from Aventura Brightline Train Station to Westchester County, returning Tue, Feb 3, priced at $503 found 18 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 March, 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 $113, 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 $113 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$112

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! (1,004 reviews)
Basic hotel with no frills

Reviewed on Jan 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)
The room was well appointed and clean. The bed was very comfortable. People need to move away from the doors when they go outside to smoke as it makes entering the building quite stinky

Reviewed on Dec 27, 2025

Get rates
Homewood Suites Stewart Airport
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,010 reviews)
Friendly staff and updated & very clean room

Reviewed on Jan 19, 2026

Get rates
Courtyard by Marriott Poughkeepsie
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 ...
9.2/10 Wonderful! (1,044 reviews)
Yes

Reviewed on Jan 16, 2026

Get rates
Hampton Inn Harriman Woodbury
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! (1,003 reviews)
Great staff. I will be back soon. I wanted to hike but couldn’t find were to access because the construction

Reviewed on Jan 20, 2026

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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 ...
8.6/10 Excellent! (1,000 reviews)
Yes

Reviewed on Jan 20, 2026

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Sleep Inn & Suites Middletown - Goshen
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE Hyde Park NY
Book a stay at this business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.6/10 Exceptional! (456 reviews)
Great ambiance. Everything was clean and downstairs lobby area was nice. Breakfast was really good.

Reviewed on Jan 18, 2026

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Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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 ...
9.4/10 Exceptional! (60 reviews)
This is a beautiful property with a very attentive staff. We enjoyed a wonderful family Christmas trip. Hope to go back soon!

Reviewed on Dec 30, 2025

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Wildflower Farms, Auberge Collection
See all 1,042 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! (1,004 reviews)
Basic hotel with no frills

Reviewed on Jan 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)
The room was well appointed and clean. The bed was very comfortable. People need to move away from the doors when they go outside to smoke as it makes entering the building quite stinky

Reviewed on Dec 27, 2025

Get rates
Homewood Suites Stewart Airport
See all 1,042 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.