Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $154

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

Breeze Airways
Tue, Jul 22 - Tue, Jul 29
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$154 Roundtrip, found 2 hours ago
$154
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Tue, Jul 22 from Raleigh - Durham Intl. to Westchester County, returning Tue, Jul 29, priced at $154 found 2 hours ago
JetBlue Airways
Sat, Aug 23 - Mon, Aug 25
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sat, Aug 23 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Mon, Aug 25, priced at $157 found 6 hours ago
JetBlue Airways
Tue, Aug 19 - Mon, Aug 25
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$159 Roundtrip, just found
$159
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Aug 19 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Mon, Aug 25, priced at $159 just found
Breeze Airways
Thu, Jul 24 - Mon, Jul 28
MCO
Orlando Intl.
HPN
Westchester County
$166 Roundtrip, found 1 hour ago
$166
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Westchester County, returning Mon, Jul 28, priced at $166 found 1 hour ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $167 found 4 days ago
Breeze Airways
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $169 found 1 hour ago
JetBlue Airways
Wed, Jul 23 - Tue, Jul 29
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Jul 23 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Tue, Jul 29, priced at $170 found 4 days ago
JetBlue Airways
Sun, Jul 20 - Tue, Jul 29
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Jul 20 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Tue, Jul 29, priced at $172 found 4 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $172 found 4 days ago
Breeze Airways
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $174 found 1 hour ago
Breeze Airways
Thu, Jul 24 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$176 Roundtrip, just found
$176
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $176 just found
JetBlue Airways
Sat, Aug 23 - Sat, Aug 23
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Aug 23 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, Aug 23, priced at $177 found 2 days ago
Delta
Wed, Aug 6 - Tue, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Aug 6 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Tue, Aug 12, priced at $197 found 1 hour ago
American Airlines
Tue, Jul 22 - Tue, Jul 29
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$198 Roundtrip, found 2 hours ago
$198
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Jul 22 from Raleigh - Durham Intl. to Westchester County, returning Tue, Jul 29, priced at $198 found 2 hours ago
American Airlines
Sat, Oct 25 - Tue, Oct 28
DEN
Denver Intl.
HPN
Westchester County
$297 Roundtrip, found 22 hours ago
$297
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Oct 25 from Denver Intl. to Westchester County, returning Tue, Oct 28, priced at $297 found 22 hours ago
American Airlines
Sat, Aug 2 - Sat, Aug 9
PHX
Sky Harbor Intl.
HPN
Westchester County
$305 Roundtrip, found 2 hours ago
$305
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Aug 2 from Sky Harbor Intl. to Westchester County, returning Sat, Aug 9, priced at $305 found 2 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 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 $154, 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 $154 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$165

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! (1,005 reviews)
"Decent site for where you’re at. Great view of the Hudson and close to lots of food options and grocery. Bed was actually very comfortable!"

Reviewed on Jul 10, 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)
"Staff was great. Easy if traveling to or from teh airport"

Reviewed on Jul 8, 2025

Get rates
Homewood Suites Stewart Airport
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 ...
9.2/10 Wonderful! (743 reviews)
"Overall had a nice stay"

Reviewed on Jul 8, 2025

Get rates
La Quinta Inn & Suites by Wyndham 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 ...
8.2/10 Very Good! (1,008 reviews)
"Unique and quiet.safe for solo travelers and with companion."

Reviewed on Jul 7, 2025

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Overlook Lodge at Bear Mountain
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 ...
9/10 Wonderful! (1,008 reviews)
"Great room and experience overall"

Reviewed on Jul 6, 2025

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Hampton Inn Harriman Woodbury
Quality Inn Poughkeepsie
Quality Inn Poughkeepsie
2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (367 reviews)
"Great, clean pool, clean rooms, no complaints. One thing to note: there is no elevator to the second floor! So if you have luggage or have walking difficulties or injuries , there’s no way to get on second floor, other than stairs. If hotel is fully booked you also may not have an option to switch ..."

Reviewed on Jul 8, 2025

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Quality Inn Poughkeepsie
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 ...
7.4/10 Good! (437 reviews)
"The room was clean and quiet. The bed was comfortable. The breakfast wasn’t good if you want healthy choices. We skipped it the second day."

Reviewed on Jun 30, 2025

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Wingate by Wyndham Fishkill
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! (1,009 reviews)
"It was easy to check in and find my room. After a long day on the road, our 11pm arrival time was accommodated for so that we could get right to bed."

Reviewed on Jul 7, 2025

Get rates
Sleep Inn & Suites Middletown - Goshen
See all 998 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! (1,005 reviews)
"Decent site for where you’re at. Great view of the Hudson and close to lots of food options and grocery. Bed was actually very comfortable!"

Reviewed on Jul 10, 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)
"Staff was great. Easy if traveling to or from teh airport"

Reviewed on Jul 8, 2025

Get rates
Homewood Suites Stewart Airport
See all 998 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.