Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $119

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

Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $119 found 4 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$124 Roundtrip, found 4 days ago
$124
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $124 found 4 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $130 found 4 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$131 Roundtrip, found 6 days ago
$131
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $131 found 6 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$136 Roundtrip, found 6 days ago
$136
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $136 found 6 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$141 Roundtrip, found 6 days ago
$141
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $141 found 6 days ago
JetBlue Airways
Thu, Sep 18 - Mon, Sep 22
MCO
Orlando Intl.
HPN
Westchester County
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 18 from Orlando Intl. to Westchester County, returning Mon, Sep 22, priced at $157 found 1 day ago
JetBlue Airways
Mon, Sep 15 - Mon, Sep 22
MCO
Orlando Intl.
HPN
Westchester County
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 15 from Orlando Intl. to Westchester County, returning Mon, Sep 22, priced at $161 found 1 day ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $164 found 5 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $169 found 5 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $174 found 5 days ago
Breeze Airways
Tue, Aug 26 - Sun, Aug 31
CHS
Charleston Intl.
HPN
Westchester County
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Aug 26 from Charleston Intl. to Westchester County, returning Sun, Aug 31, priced at $177 found 4 days ago
JetBlue Airways
Thu, Sep 18 - Sat, Sep 20
MCO
Orlando Intl.
HPN
Westchester County
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 18 from Orlando Intl. to Westchester County, returning Sat, Sep 20, priced at $177 found 1 day ago
Delta
Tue, Aug 26 - Sun, Aug 31
CHS
Charleston Intl.
HPN
Westchester County
$220 Roundtrip, found 4 days ago
$220
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 26 from Charleston Intl. to Westchester County, returning Sun, Aug 31, priced at $220 found 4 days ago
American Airlines
Thu, Sep 18 - Tue, Sep 23
MCO
Orlando Intl.
HPN
Westchester County
$225 Roundtrip, found 1 day ago
$225
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 18 from Orlando Intl. to Westchester County, returning Tue, Sep 23, priced at $225 found 1 day ago
Breeze Airways
Mon, Aug 18 - Fri, Aug 22
CHS
Charleston Intl.
SWF
Stewart Intl.
$238 Roundtrip, found 4 days ago
$238
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Aug 18 from Charleston Intl. to Stewart Intl., returning Fri, Aug 22, priced at $238 found 4 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 $119, 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 $119 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$160

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! (1,004 reviews)
"Really lovely staff!"

Reviewed on Aug 13, 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! (1,000 reviews)
"The desk staff was excellent"

Reviewed on Aug 11, 2025

Get rates
Homewood Suites Stewart Airport
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (512 reviews)
"Comfortable place to stay"

Reviewed on Aug 7, 2025

Get rates
The Crossroads Hotel, Newburgh
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! (1,007 reviews)
"Stay was great. Staff was kind, courteous and helpful. The room was clean and spacious. The complimentary breakfast was way more then I expected and was excellent. I will stay there again when we come back in October."

Reviewed on Aug 15, 2025

Get rates
Sleep Inn & Suites Middletown - Goshen
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
Stay at this 5-star 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! (51 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

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Wildflower Farms, Auberge Resorts Collection
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! (1,002 reviews)
"Bed was comfortable and room was clean and good size Thank you!will come back"

Reviewed on Aug 13, 2025

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Overlook Lodge at Bear Mountain
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! (472 reviews)
"Beautiful renovated hotel. We loved our stay here"

Reviewed on Aug 10, 2025

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Wingate by Wyndham Fishkill
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! (1,005 reviews)
"The hotel is in a busy BUT very secluded being in the back of the main road. It is beyond clean. Room was spacious and very comfortable. Breakfast was good. Coffee and tea available 24 hrs. Staff very nice and knowledgeable. Only complaint, you do need a car to go to the outlets. It says walking ..."

Reviewed on Aug 15, 2025

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Hampton Inn Harriman Woodbury
See all 981 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! (1,004 reviews)
"Really lovely staff!"

Reviewed on Aug 13, 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! (1,000 reviews)
"The desk staff was excellent"

Reviewed on Aug 11, 2025

Get rates
Homewood Suites Stewart Airport
See all 981 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.