Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $99

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

JetBlue Airways
Mon, Oct 27 - Fri, Oct 31
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$99 Roundtrip, found 8 hours ago
$99
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Mon, Oct 27 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Fri, Oct 31, priced at $99 found 8 hours ago
JetBlue Airways
Fri, Sep 26 - Sun, Sep 28
TPA
Tampa Intl.
HPN
Westchester County
$99 Roundtrip, found 13 hours ago
$99
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Fri, Sep 26 from Tampa Intl. to Westchester County, returning Sun, Sep 28, priced at $99 found 13 hours ago
JetBlue Airways
Sat, Oct 11 - Sat, Oct 18
TPA
Tampa Intl.
HPN
Westchester County
$109 Roundtrip, found 4 days ago
$109
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Oct 11 from Tampa Intl. to Westchester County, returning Sat, Oct 18, priced at $109 found 4 days ago
JetBlue Airways
Fri, Sep 12 - Mon, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Sep 12 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Mon, Sep 15, priced at $117 found 5 days ago
JetBlue Airways
Fri, Sep 26 - Sat, Sep 27
TPA
Tampa Intl.
HPN
Westchester County
$119 Roundtrip, found 23 hours ago
$119
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Sep 26 from Tampa Intl. to Westchester County, returning Sat, Sep 27, priced at $119 found 23 hours ago
JetBlue Airways
Tue, Oct 21 - Thu, Oct 23
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Thu, Oct 23, priced at $130 found 5 days ago
JetBlue Airways
Fri, Sep 12 - Sat, Sep 13
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Sep 12 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, Sep 13, priced at $137 found 5 days ago
Breeze Airways
Wed, Sep 24 - Mon, Sep 29
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$156 Roundtrip, found 12 hours ago
$156
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Sep 24 from Raleigh - Durham Intl. to Westchester County, returning Mon, Sep 29, priced at $156 found 12 hours ago
American Airlines
Sat, Sep 27 - Tue, Sep 30
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 27 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 30, priced at $159 found 2 days ago
Delta
Sat, Sep 27 - Tue, Sep 30
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 27 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 30, priced at $179 found 2 days ago
Delta
Fri, Oct 3 - Sat, Oct 11
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Oct 3 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Sat, Oct 11, priced at $229 found 3 days ago
Breeze Airways
Wed, Sep 24 - Mon, Sep 29
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$261 Roundtrip, found 12 hours ago
$261
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Sep 24 from Raleigh - Durham Intl. to Westchester County, returning Mon, Sep 29, priced at $261 found 12 hours ago
American Airlines
Tue, Oct 14 - Tue, Oct 14
DFW
Dallas-Fort Worth Intl.
HPN
Westchester County
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 14 from Dallas-Fort Worth Intl. to Westchester County, returning Tue, Oct 14, priced at $321 found 1 day ago
American Airlines
Wed, Sep 17 - Tue, Sep 23
LAX
Los Angeles Intl.
HPN
Westchester County
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 17 from Los Angeles Intl. to Westchester County, returning Tue, Sep 23, priced at $349 found 1 day ago
Delta
Tue, Oct 14 - Tue, Oct 14
DAL
Love Field
HPN
Westchester County
$394 Roundtrip, found 1 day ago
$394
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 14 from Love Field to Westchester County, returning Tue, Oct 14, priced at $394 found 1 day ago
Breeze Airways
Thu, Oct 9 - Fri, Oct 17
TPA
Tampa Intl.
SWF
Stewart Intl.
$582 Roundtrip, found 4 days ago
$582
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Oct 9 from Tampa Intl. to Stewart Intl., returning Fri, Oct 17, priced at $582 found 4 days 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 $99, 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 $99 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Airlines serving
American Airlines, Delta, Frontier Airlines, Spirit Airlines, United
Number of airlines serving
5
Roundtrip price
$349
Popular airline
Spirit Airlines

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 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 ...
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Homewood Suites Stewart Airport
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
Get rates
The Crossroads Hotel, Newburgh
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 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 ...
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Overlook Lodge at Bear Mountain
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Lake and Tuthilltown Spirits are ...
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Wildflower Farms, Auberge Resorts Collection
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 ...
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Hampton Inn Harriman Woodbury
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 ...
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La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 978 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 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 ...
Get rates
Homewood Suites Stewart Airport
See all 978 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.