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New Windsor

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New Windsor Flights as Low as $138

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

Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $138 found 6 days ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $143 found 6 days ago
Breeze Airways
Sun, May 31 - Sun, Jun 14
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, May 31 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jun 14, priced at $148 found 1 day ago
Breeze Airways
Sun, May 31 - Sun, Jun 14
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, May 31 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jun 14, priced at $153 found 1 day ago
Breeze Airways
Fri, Apr 3 - Wed, Apr 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 3 from Raleigh - Durham Intl. to Westchester County, returning Wed, Apr 8, priced at $157 found 2 days ago
Breeze Airways
Sun, May 31 - Sun, Jun 14
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, May 31 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jun 14, priced at $158 found 1 day ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $159 found 5 days ago
Breeze Airways
Fri, Apr 3 - Wed, Apr 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 3 from Raleigh - Durham Intl. to Westchester County, returning Wed, Apr 8, priced at $162 found 2 days ago
Breeze Airways
Tue, May 19 - Sat, May 30
MCO
Orlando Intl.
HPN
Westchester County
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, May 19 from Orlando Intl. to Westchester County, returning Sat, May 30, priced at $163 found 2 days ago
Breeze Airways
Fri, Apr 3 - Wed, Apr 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 3 from Raleigh - Durham Intl. to Westchester County, returning Wed, Apr 8, priced at $167 found 2 days ago
Breeze Airways
Thu, May 14 - Mon, May 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, May 14 from Orlando Intl. to Stewart Intl., returning Mon, May 18, priced at $168 found 2 days ago
Breeze Airways
Wed, Jun 10 - Wed, Jun 17
TPA
Tampa Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 3 days ago
$195
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jun 10 from Tampa Intl. to Stewart Intl., returning Wed, Jun 17, priced at $195 found 3 days ago
JetBlue Airways
Wed, May 13 - Tue, May 19
MCO
Orlando Intl.
HPN
Westchester County
$216 Roundtrip, found 3 days ago
$216
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, May 13 from Orlando Intl. to Westchester County, returning Tue, May 19, priced at $216 found 3 days ago
Delta
Wed, Apr 22 - Tue, Apr 28
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$226 Roundtrip, found 3 days ago
$226
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 22 from Raleigh - Durham Intl. to Westchester County, returning Tue, Apr 28, priced at $226 found 3 days ago
Delta
Wed, Apr 15 - Mon, Apr 20
TPA
Tampa Intl.
HPN
Westchester County
$227 Roundtrip, found 2 days ago
$227
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Tampa Intl. to Westchester County, returning Mon, Apr 20, priced at $227 found 2 days ago
American Airlines
Fri, Apr 3 - Wed, Apr 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$236 Roundtrip, found 2 days ago
$236
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Apr 3 from Raleigh - Durham Intl. to Westchester County, returning Wed, Apr 8, priced at $236 found 2 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 June, 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 $138, 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 $138 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$163

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! (1,000 reviews)
The place is clean every time I come and outstanding customer service

Reviewed on Mar 16, 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)
Good

Reviewed on Feb 26, 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 ...
8.6/10 Excellent! (1,003 reviews)
Clean room, safe and staff is courteous

Reviewed on Mar 19, 2026

Get rates
Sleep Inn & Suites Middletown - Goshen
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 Central Valley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,074 reviews)
It was nice

Reviewed on Mar 20, 2026

Get rates
Hampton Inn Harriman Woodbury
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
9/10 Wonderful! (1,001 reviews)
It was a nice stay, no complaints. We will definitely stay here again next time we are in the area!

Reviewed on Mar 17, 2026

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Hampton Inn & Suites Poughkeepsie
Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

3 out of 5
17 Westage Drive Fishkill NY
Book a stay at this business-friendly hotel in Fishkill. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.8/10 Excellent! (756 reviews)
Staff was very nice . Gave us water bottles , and i loved that they didn’t come knocking on the door as soon as it was checkout time

Reviewed on Mar 18, 2026

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Courtyard by Marriott Fishkill
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing Middletown NY
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (1,000 reviews)
Clean room , very nice place. However when I was booking I paid for breakfast. When I got there the front desk told me that they didn’t see it on the reservation

Reviewed on Mar 16, 2026

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Courtyard by Marriott 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)
We stayed at the cottages which were clean and welcoming. The only thing to keep in mind is that the common area IS common, so if you don’t want to socialize, it might not be the space for you. We had a party with us that all knew each other (and we were the only room who didn’t) and they hung out ...

Reviewed on Mar 16, 2026

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Overlook Lodge at Bear Mountain
See all 1,025 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! (1,000 reviews)
The place is clean every time I come and outstanding customer service

Reviewed on Mar 16, 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)
Good

Reviewed on Feb 26, 2026

Get rates
Homewood Suites Stewart Airport
See all 1,025 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.