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New Windsor

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New Windsor Flights as Low as $217

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

JetBlue Airways
Tue, Aug 25 - Wed, Sep 2
PBI
Palm Beach Intl.
HPN
Westchester County
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Palm Beach Intl. to Westchester County, returning Wed, Sep 2, priced at $217 found 3 days ago
JetBlue Airways
Sat, Aug 1 - Sat, Aug 8
PBI
Palm Beach Intl.
HPN
Westchester County
$222 Roundtrip, found 23 hours ago
$222
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Sat, Aug 1 from Palm Beach Intl. to Westchester County, returning Sat, Aug 8, priced at $222 found 23 hours ago
Delta
Tue, Aug 25 - Sat, Sep 5
PBI
Palm Beach Intl.
HPN
Westchester County
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 25 from Palm Beach Intl. to Westchester County, returning Sat, Sep 5, priced at $227 found 3 days ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 18
PBI
Palm Beach Intl.
HPN
Westchester County
$232 Roundtrip, found 3 days ago
$232
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Palm Beach Intl. to Westchester County, returning Tue, Aug 18, priced at $232 found 3 days ago
Delta
Tue, Aug 25 - Sat, Sep 5
PBI
Palm Beach Intl.
HPN
Westchester County
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 25 from Palm Beach Intl. to Westchester County, returning Sat, Sep 5, priced at $237 found 3 days ago
American Airlines
Tue, Aug 25 - Sat, Sep 5
PBI
Palm Beach Intl.
HPN
Westchester County
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 25 from Palm Beach Intl. to Westchester County, returning Sat, Sep 5, priced at $237 found 3 days ago
Delta
Tue, Aug 4 - Tue, Aug 18
PBI
Palm Beach Intl.
HPN
Westchester County
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 4 from Palm Beach Intl. to Westchester County, returning Tue, Aug 18, priced at $242 found 3 days ago
JetBlue Airways
Tue, Jul 14 - Sat, Jul 18
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jul 14 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, Jul 18, priced at $243 found 2 days ago
Delta
Sat, Jul 11 - Tue, Jul 14
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$284 Roundtrip, found 13 hours ago
$284
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Jul 11 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Tue, Jul 14, priced at $284 found 13 hours ago
Breeze Airways
Mon, Jul 27 - Mon, Aug 10
PBI
Palm Beach Intl.
HPN
Westchester County
$301 Roundtrip, found 6 days ago
$301
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Jul 27 from Palm Beach Intl. to Westchester County, returning Mon, Aug 10, priced at $301 found 6 days ago
Delta
Wed, Jul 1 - Wed, Jul 8
DTW
Detroit Metropolitan Wayne County
HPN
Westchester County
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 1 from Detroit Metropolitan Wayne County to Westchester County, returning Wed, Jul 8, priced at $351 found 3 days ago
American Airlines
Tue, Oct 13 - Sat, Oct 17
CLT
Charlotte-Douglas Intl.
HPN
Westchester County
$387 Roundtrip, found 9 hours ago
$387
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Oct 13 from Charlotte-Douglas Intl. to Westchester County, returning Sat, Oct 17, priced at $387 found 9 hours ago
Delta
Tue, Jun 30 - Sat, Jul 4
MSN
Dane County Regional
HPN
Westchester County
$456 Roundtrip, found 13 hours ago
$456
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Jun 30 from Dane County Regional to Westchester County, returning Sat, Jul 4, priced at $456 found 13 hours ago
American Airlines
Wed, Jul 1 - Sat, Jul 4
LAX
Los Angeles Intl.
HPN
Westchester County
$479 Roundtrip, found 13 hours ago
$479
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Los Angeles Intl. to Westchester County, returning Sat, Jul 4, priced at $479 found 13 hours ago
Breeze Airways
Tue, Aug 11 - Wed, Aug 26
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$519 Roundtrip, found 5 days ago
$519
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Aug 11 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Wed, Aug 26, priced at $519 found 5 days ago
Breeze Airways
Tue, Jul 7 - Sat, Jul 11
PBI
Palm Beach Intl.
SWF
Stewart Intl.
$573 Roundtrip, found 5 days ago
$573
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Jul 7 from Palm Beach Intl. to Stewart Intl., returning Sat, Jul 11, priced at $573 found 5 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 August, 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 $217, 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 $217 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$217

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! (1,002 reviews)
"No frills, good price point, clean."

Reviewed on Jun 26, 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 ...
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Homewood Suites Stewart Airport
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! (1,008 reviews)
"Large room,very clean,exactly what we wanted"

Reviewed on Jun 27, 2026

Get rates
Hyatt Place Poughkeepsie / Hudson Valley
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! (145 reviews)
"The room was clean. The mattress is very comfortable. Staff was nice. It’s a cheap hotel so it’s not fancy but it has everything you need and it’s clean."

Reviewed on Jun 26, 2026

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Spark by Hilton Fishkill
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! (1,004 reviews)
"everything was amazing , my husband and I really enjoyed our time there"

Reviewed on Jun 26, 2026

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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 ...
8.8/10 Excellent! (1,042 reviews)
"Clean room loved my stay with my family the kids enjoy the pool a lot of things close by to do too…"

Reviewed on Jun 25, 2026

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Sleep Inn & Suites Middletown - Goshen
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 Preserve Visitor Center and Mohonk ...
9.4/10 Exceptional! (67 reviews)
"Amazing stay! Will be back"

Reviewed on May 16, 2026

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Wildflower Farms, Auberge Collection
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.8/10 Good! (1,001 reviews)
"Clean, nice staff and easy to navigate. Comfortable beds with plenty of pillows. Could have done without 730 am bagpipes outside room, but otherwise nice."

Reviewed on Jun 27, 2026

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SureStay Plus Hotel by Best Western Highland Poughkeepsie
See all 1,049 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! (1,002 reviews)
"No frills, good price point, clean."

Reviewed on Jun 26, 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 ...
Get rates
Homewood Suites Stewart Airport
See all 1,049 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.