Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $161

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

Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$161 Roundtrip, found 21 hours ago
$161
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $161 found 21 hours ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$164 Roundtrip, found 21 hours ago
$164
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $164 found 21 hours ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$167 Roundtrip, found 21 hours ago
$167
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $167 found 21 hours ago
JetBlue Airways
Sat, Jul 19 - Mon, Jul 21
MCO
Orlando Intl.
HPN
Westchester County
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Jul 19 from Orlando Intl. to Westchester County, returning Mon, Jul 21, priced at $170 found 2 days ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$172 Roundtrip, found 21 hours ago
$172
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $172 found 21 hours ago
Breeze Airways
Tue, Jul 15 - Mon, Jul 21
CHS
Charleston Intl.
HPN
Westchester County
$175 Roundtrip, found 21 hours ago
$175
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Tue, Jul 15 from Charleston Intl. to Westchester County, returning Mon, Jul 21, priced at $175 found 21 hours ago
Breeze Airways
Tue, Jul 15 - Mon, Jul 21
CHS
Charleston Intl.
HPN
Westchester County
$180 Roundtrip, found 21 hours ago
$180
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Tue, Jul 15 from Charleston Intl. to Westchester County, returning Mon, Jul 21, priced at $180 found 21 hours ago
JetBlue Airways
Tue, Jul 22 - Tue, Jul 22
MCO
Orlando Intl.
HPN
Westchester County
$185 Roundtrip, found 9 hours ago
$185
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Tue, Jul 22, priced at $185 found 9 hours ago
American Airlines
Tue, Jul 22 - Tue, Jul 22
MCO
Orlando Intl.
HPN
Westchester County
$195 Roundtrip, found 9 hours ago
$195
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Tue, Jul 22, priced at $195 found 9 hours ago
Delta
Tue, Aug 26 - Wed, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Wed, Sep 3, priced at $197 found 1 hour ago
Breeze Airways
Thu, Jun 26 - Tue, Jul 1
TPA
Tampa Intl.
HPN
Westchester County
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Tampa Intl. to Westchester County, returning Tue, Jul 1, priced at $201 found 2 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $206 found 4 days ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $224 found 1 day ago
JetBlue Airways
Tue, Sep 16 - Fri, Sep 19
LAX
Los Angeles Intl.
HPN
Westchester County
$293 Roundtrip, found 18 hours ago
$293
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Los Angeles Intl. to Westchester County, returning Fri, Sep 19, priced at $293 found 18 hours ago
American Airlines
Mon, Jun 30 - Mon, Jun 30
DFW
Dallas-Fort Worth Intl.
HPN
Westchester County
$304 Roundtrip, found 19 hours ago
$304
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Mon, Jun 30 from Dallas-Fort Worth Intl. to Westchester County, returning Mon, Jun 30, priced at $304 found 19 hours ago
Delta
Wed, Jun 25 - Fri, Jul 4
DAL
Love Field
HPN
Westchester County
$331 Roundtrip, found 3 days ago
$331
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 25 from Love Field to Westchester County, returning Fri, Jul 4, priced at $331 found 3 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 July, 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 $161, 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 $161 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$161

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! (1,003 reviews)
"The room was nice, however some of the business should have been replaced or repaired. The staff was great, very friendly and helpful. The laundry facilities and computer station need immediate attention."

Reviewed on Jun 11, 2025

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 ...
9.2/10 Wonderful! (1,001 reviews)
"Great room nice price"

Reviewed on Jun 9, 2025

Get rates
Homewood Suites Stewart Airport
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,007 reviews)
"I really liked the location. So close to highway exit, easy to park. Close to shops and resturants and they even have a bar with snack (finger food)."

Reviewed on Jun 12, 2025

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HYATT house Fishkill/Poughkeepsie
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 ...
8.6/10 Excellent! (1,002 reviews)
"Great customer service"

Reviewed on Jun 11, 2025

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Hampton Inn & Suites Poughkeepsie
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 ...
8.2/10 Very Good! (1,000 reviews)
"조용히 휴식하기에 좋은 곳입니다. 2층에있는 레스토랑이 훌륭합니다."

Reviewed on Jun 8, 2025

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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 ...
8.4/10 Very Good! (1,002 reviews)
"Convenient for what I needed. Breakfast was a nice feature."

Reviewed on Jun 11, 2025

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Sleep Inn & Suites Middletown - Goshen
Wingate by Wyndham Fishkill
Wingate by Wyndham Fishkill
3 out of 5
20 Schuyler Blvd, Fishkill, NY
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (408 reviews)
Just right
"Simple but everything you need. Very comfy bed."

Reviewed on Jun 10, 2025

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Wingate by Wyndham Fishkill
Super 8 by Wyndham Middletown
Super 8 by Wyndham Middletown
2.5 out of 5
563 Route 211 E, I-84 Exit 4W Rt 17 Exit 120, Middletown, NY
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.2/10 (1,001 reviews)
"Quick and friendly"

Reviewed on May 24, 2025

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Super 8 by Wyndham Middletown
See all 995 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! (1,003 reviews)
"The room was nice, however some of the business should have been replaced or repaired. The staff was great, very friendly and helpful. The laundry facilities and computer station need immediate attention."

Reviewed on Jun 11, 2025

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 ...
9.2/10 Wonderful! (1,001 reviews)
"Great room nice price"

Reviewed on Jun 9, 2025

Get rates
Homewood Suites Stewart Airport
See all 995 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.