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New Windsor

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New Windsor Flights as Low as $82

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

Breeze Airways
Tue, Sep 22 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$82 Roundtrip, found 7 hours ago
$82
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Tue, Sep 22 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 26, priced at $82 found 7 hours ago
Breeze Airways
Tue, Sep 22 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$87 Roundtrip, found 7 hours ago
$87
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Tue, Sep 22 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 26, priced at $87 found 7 hours ago
Breeze Airways
Tue, Sep 22 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$92 Roundtrip, found 7 hours ago
$92
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Tue, Sep 22 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 26, priced at $92 found 7 hours ago
Breeze Airways
Tue, Aug 11 - Wed, Aug 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 11 from Raleigh - Durham Intl. to Westchester County, returning Wed, Aug 19, priced at $132 found 3 days ago
Breeze Airways
Tue, Aug 11 - Wed, Aug 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 11 from Raleigh - Durham Intl. to Westchester County, returning Wed, Aug 19, priced at $137 found 3 days ago
Breeze Airways
Tue, Aug 11 - Wed, Aug 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 11 from Raleigh - Durham Intl. to Westchester County, returning Wed, Aug 19, priced at $142 found 3 days ago
Breeze Airways
Thu, Aug 13 - Sun, Aug 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 13 from Raleigh - Durham Intl. to Westchester County, returning Sun, Aug 16, priced at $153 found 6 days ago
Breeze Airways
Thu, Aug 13 - Sun, Aug 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 13 from Raleigh - Durham Intl. to Westchester County, returning Sun, Aug 16, priced at $158 found 6 days ago
Breeze Airways
Tue, Jun 30 - Sat, Jul 4
MCO
Orlando Intl.
HPN
Westchester County
$162 Roundtrip, found 12 hours ago
$162
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Tue, Jun 30 from Orlando Intl. to Westchester County, returning Sat, Jul 4, priced at $162 found 12 hours ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $180 found 3 days ago
Breeze Airways
Wed, Sep 2 - Sat, Sep 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Stewart Intl., returning Sat, Sep 5, priced at $182 found 6 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$185 Roundtrip, found 6 days ago
$185
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $185 found 6 days ago
JetBlue Airways
Tue, Jun 23 - Thu, Jul 9
MCO
Orlando Intl.
HPN
Westchester County
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jun 23 from Orlando Intl. to Westchester County, returning Thu, Jul 9, priced at $207 found 6 days ago
American Airlines
Tue, Sep 22 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$211 Roundtrip, found 7 hours ago
$211
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Sep 22 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 26, priced at $211 found 7 hours ago
Delta
Tue, Aug 11 - Wed, Aug 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 11 from Raleigh - Durham Intl. to Westchester County, returning Wed, Aug 19, priced at $219 found 3 days ago
Delta
Sat, Jun 13 - Sat, Jun 13
TPA
Tampa Intl.
HPN
Westchester County
$253 Roundtrip, found 6 days ago
$253
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jun 13 from Tampa Intl. to Westchester County, returning Sat, Jun 13, priced at $253 found 6 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 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 $82, 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 $82 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$81

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! (1,004 reviews)
"The staff was awesome however the hotel hallways and our room had a weird odor and we found multiple bugs in the room. Was not impressed at all and will not be back."

Reviewed on Jun 4, 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! (1,001 reviews)
"Kathy at the Front Desk and all of the personnel at this site were very friendly and professional."

Reviewed on May 28, 2026

Get rates
Homewood Suites Stewart Airport
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (119 reviews)
"New and refurbished"

Reviewed on Jun 4, 2026

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Spark by Hilton Fishkill
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! (1,010 reviews)
"I loved everything about this hotel EXCEPT the beds. They are WAY TOO SOFT."

Reviewed on Jun 4, 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 ...
8.4/10 Very Good! (1,011 reviews)
"Fantastic place, old, well kept. No WiFi in overlook lodge for 3 days."

Reviewed on May 31, 2026

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Overlook Lodge at Bear Mountain
Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course ...
6.6/10 (1,000 reviews)
"THANK YOU TO EVERYONE THAT WORK'S HERE JUST KNOW THAT YOU ALL ARE AMAZING THANK YOU"

Reviewed on Jun 1, 2026

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Studio 6 Extended Stay Fishkill Route 9 NY
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 Mohonk Lake and Tuthilltown Spirits are ...
9.4/10 Exceptional! (67 reviews)
"Amazing stay! Will be back"

Reviewed on May 16, 2026

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Wildflower Farms, Auberge Collection
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd Newburgh NY
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (770 reviews)
"Very clean room parking was safe and easy and the staff was helpful"

Reviewed on Jun 4, 2026

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The Crossroads Hotel, Newburgh
See all 1,048 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! (1,004 reviews)
"The staff was awesome however the hotel hallways and our room had a weird odor and we found multiple bugs in the room. Was not impressed at all and will not be back."

Reviewed on Jun 4, 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! (1,001 reviews)
"Kathy at the Front Desk and all of the personnel at this site were very friendly and professional."

Reviewed on May 28, 2026

Get rates
Homewood Suites Stewart Airport
See all 1,048 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.