Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $164

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

Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $164 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $169 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $174 found 2 days ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $181 found 15 hours ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$191 Roundtrip, found 15 hours ago
$191
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $191 found 15 hours ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $195 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $200 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$205 Roundtrip, found 2 days ago
$205
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $205 found 2 days ago
JetBlue Airways
Tue, Jun 17 - Tue, Jun 24
MCO
Orlando Intl.
HPN
Westchester County
$221 Roundtrip, found 5 days ago
$221
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Jun 17 from Orlando Intl. to Westchester County, returning Tue, Jun 24, priced at $221 found 5 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $225 found 4 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $230 found 4 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$231 Roundtrip, found 3 days ago
$231
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $231 found 3 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $235 found 4 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $240 found 4 days ago
Delta
Tue, Jun 17 - Tue, Jun 24
MCO
Orlando Intl.
HPN
Westchester County
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 17 from Orlando Intl. to Westchester County, returning Tue, Jun 24, priced at $241 found 5 days ago
American Airlines
Tue, Jun 17 - Tue, Jun 24
MCO
Orlando Intl.
HPN
Westchester County
$266 Roundtrip, found 5 days ago
$266
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jun 17 from Orlando Intl. to Westchester County, returning Tue, Jun 24, priced at $266 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 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 $164, 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 $164 right now, why wait?

New Windsor Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
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
The price is $127 per night from May 11 to May 12
$127
includes taxes & fees
May 11 - May 12
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! (1,001 reviews)
Great Staff! Exceptionally clean
"Although this is an older property, the room was extremely clean. I did not check in until closet to 10 pm the evening of 4/26 and there was an issue with my reservation, my fault totally! I had inadvertently confirmed my stay for the night before. The gentleman at the front desk ( his name escapes ..."

Reviewed on Apr 28, 2025

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
The price is $182 per night from May 26 to May 27
$182
includes taxes & fees
May 26 - May 27
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)
"Excellent service very clean will definitely stay again!!!"

Reviewed on Apr 27, 2025

Homewood Suites Stewart Airport
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
The price is $140 per night from May 4 to May 5
$140
includes taxes & fees
May 4 - May 5
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! (1,001 reviews)
"The staff, room and property were lovely. The view from the porch? Spectacular !!!"

Reviewed on Apr 28, 2025

Overlook Lodge at Bear Mountain
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
The price is $150 per night from May 6 to May 7
$150
includes taxes & fees
May 6 - May 7
Book a stay at this 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! (687 reviews)
"The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again."

Reviewed on Apr 29, 2025

La Quinta Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
The price is $134 per night from May 26 to May 27
$134
includes taxes & fees
May 26 - May 27
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! (1,000 reviews)
"Great property close to legoland. We saw some ants coming out from an outlet into our room on the second day. We quickly made sure to put our food items in the fridge."

Reviewed on Apr 28, 2025

Sleep Inn & Suites Middletown - Goshen
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $124 per night from May 11 to May 12
$124
includes taxes & fees
May 11 - May 12
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! (1,000 reviews)
"Super clean"

Reviewed on Apr 28, 2025

HYATT house Fishkill/Poughkeepsie
Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury
2.5 out of 5
60 Centre Dr, Central Valley, NY
The price is $161 per night from May 4 to May 5
$161
includes taxes & fees
May 4 - May 5
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! (1,001 reviews)
"Clean, comfortable. Good value."

Reviewed on Apr 27, 2025

Hampton Inn Harriman Woodbury
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
The price is $130 per night from May 26 to May 27
$130
includes taxes & fees
May 26 - May 27
Stay at this 3-star hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (875 reviews)
"The room was not cleaned between our 2 night stay"

Reviewed on Apr 26, 2025

Courtyard by Marriott Middletown Goshen
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
The price is $127 per night from May 11 to May 12
$127
includes taxes & fees
May 11 - May 12
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! (1,001 reviews)
Great Staff! Exceptionally clean
"Although this is an older property, the room was extremely clean. I did not check in until closet to 10 pm the evening of 4/26 and there was an issue with my reservation, my fault totally! I had inadvertently confirmed my stay for the night before. The gentleman at the front desk ( his name escapes ..."

Reviewed on Apr 28, 2025

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
The price is $182 per night from May 26 to May 27
$182
includes taxes & fees
May 26 - May 27
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)
"Excellent service very clean will definitely stay again!!!"

Reviewed on Apr 27, 2025

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.