Search Cheap Flights to
New Windsor

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New Windsor Flights as Low as $173

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.
$173 Roundtrip, found 3 days ago
$173
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $173 found 3 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $178 found 3 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $183 found 3 days ago
Breeze Airways
Tue, Mar 11 - Mon, Mar 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$212 Roundtrip, found 5 days ago
$212
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Mar 11 from Orlando Intl. to Stewart Intl., returning Mon, Mar 17, priced at $212 found 5 days ago
Breeze Airways
Tue, Mar 11 - Thu, Mar 13
MCO
Orlando Intl.
SWF
Stewart Intl.
$214 Roundtrip, found 12 hours ago
$214
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Tue, Mar 11 from Orlando Intl. to Stewart Intl., returning Thu, Mar 13, priced at $214 found 12 hours ago
Breeze Airways
Tue, Mar 11 - Mon, Mar 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Mar 11 from Orlando Intl. to Stewart Intl., returning Mon, Mar 17, priced at $222 found 5 days ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 20
MCO
Orlando Intl.
HPN
Westchester County
$223 Roundtrip, found 4 days ago
$223
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Westchester County, returning Sun, Jul 20, priced at $223 found 4 days ago
Breeze Airways
Tue, Mar 11 - Thu, Mar 13
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 12 hours ago
$224
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Tue, Mar 11 from Orlando Intl. to Stewart Intl., returning Thu, Mar 13, priced at $224 found 12 hours ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 20
MCO
Orlando Intl.
HPN
Westchester County
$228 Roundtrip, found 4 days ago
$228
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Westchester County, returning Sun, Jul 20, priced at $228 found 4 days ago
Breeze Airways
Tue, Mar 11 - Mon, Mar 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Mar 11 from Orlando Intl. to Stewart Intl., returning Mon, Mar 17, priced at $235 found 4 days ago
Breeze Airways
Tue, Mar 11 - Mon, Mar 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Mar 11 from Orlando Intl. to Stewart Intl., returning Mon, Mar 17, priced at $245 found 4 days ago
JetBlue Airways
Tue, Jul 8 - Thu, Jul 17
MCO
Orlando Intl.
HPN
Westchester County
$258 Roundtrip, found 4 days ago
$258
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Jul 8 from Orlando Intl. to Westchester County, returning Thu, Jul 17, priced at $258 found 4 days ago
JetBlue Airways
Thu, Jul 10 - Sun, Jul 20
MCO
Orlando Intl.
HPN
Westchester County
$268 Roundtrip, found 4 days ago
$268
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Jul 10 from Orlando Intl. to Westchester County, returning Sun, Jul 20, priced at $268 found 4 days ago
American Airlines
Thu, Jul 10 - Sun, Jul 20
MCO
Orlando Intl.
HPN
Westchester County
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Jul 10 from Orlando Intl. to Westchester County, returning Sun, Jul 20, priced at $277 found 4 days ago
JetBlue Airways
Thu, Jul 10 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$278 Roundtrip, found 5 days ago
$278
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Jul 10 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $278 found 5 days ago
Delta
Sat, Jul 5 - Sat, Jul 19
MCO
Orlando Intl.
HPN
Westchester County
$389 Roundtrip, found 5 days ago
$389
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 5 from Orlando Intl. to Westchester County, returning Sat, Jul 19, priced at $389 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 $173, 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 $173 right now, why wait?

New Windsor Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$142

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 $112 per night from Mar 11 to Mar 12
$112
includes taxes & fees
Mar 11 - Mar 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! (1,007 reviews)
"Best place to stay"

Reviewed on Mar 4, 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 $134 per night from Mar 16 to Mar 17
$134
includes taxes & fees
Mar 16 - Mar 17
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! (980 reviews)
Highly recommend and will visit again!
"Wow! From check in to check out we have super friendly staff, the rooms were so clean and aircon/heat worked well. Beds and sofa bed were comfy, breakfast buffet had a great selection for many different eating lifestyles. Plenty of seating and lounging areas. Pool was cleaning and hot tub was cozy! ..."

Reviewed on Mar 6, 2025

Homewood Suites Stewart Airport
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $117 per night from Mar 17 to Mar 18
$117
includes taxes & fees
Mar 17 - Mar 18
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! (1,017 reviews)
"Awesome"

Reviewed on Mar 8, 2025

HYATT house Fishkill/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
The price is $114 per night from Mar 11 to Mar 12
$114
includes taxes & fees
Mar 11 - Mar 12
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 ...
8/10 Very Good! (1,008 reviews)
Wonderful stay!
"Great stay in one of the cozy stone lodges. We stayed just one night but we met the other people staying our lodge and had a nice get together in front of the fire in the common room. Room was very clean; bathroom has an odd configuration. You can barely open the door to get in it (why not make the ..."

Reviewed on Mar 3, 2025

Overlook Lodge at Bear Mountain
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
The price is $849 per night from Mar 13 to Mar 14
$849
includes taxes & fees
Mar 13 - Mar 14
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery ...
9.4/10 Exceptional! (48 reviews)
"Its a beautiful property and some of the best staff and service. Looking forward to be back soon"

Reviewed on Mar 4, 2025

Wildflower Farms, Auberge Resorts Collection
Hyatt Place Poughkeepsie / Hudson Valley
Hyatt Place Poughkeepsie / Hudson Valley
3 out of 5
2165 South Road, Poughkeepsie, NY
The price is $138 per night from Apr 1 to Apr 2
$138
includes taxes & fees
Apr 1 - Apr 2
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,010 reviews)
Great stay
"Staff was friendly and helpful. The breakfast was great. Everything was clean and well maintained."

Reviewed on Mar 3, 2025

Hyatt Place Poughkeepsie / Hudson Valley
Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury
2.5 out of 5
60 Centre Dr, Central Valley, NY
The price is $125 per night from Mar 17 to Mar 18
$125
includes taxes & fees
Mar 17 - Mar 18
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! (1,009 reviews)
"Clean and nice rooms!"

Reviewed on Mar 7, 2025

Hampton Inn Harriman Woodbury
Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHG
2.5 out of 5
2 Bryle Place, Chester, NY
The price is $141 per night from Apr 6 to Apr 7
$141
includes taxes & fees
Apr 6 - Apr 7
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,007 reviews)
"The place was clean complementary breakfast was ok, i really enjoy my stay."

Reviewed on Mar 9, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
See all 971 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 $112 per night from Mar 11 to Mar 12
$112
includes taxes & fees
Mar 11 - Mar 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! (1,007 reviews)
"Best place to stay"

Reviewed on Mar 4, 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 $134 per night from Mar 16 to Mar 17
$134
includes taxes & fees
Mar 16 - Mar 17
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! (980 reviews)
Highly recommend and will visit again!
"Wow! From check in to check out we have super friendly staff, the rooms were so clean and aircon/heat worked well. Beds and sofa bed were comfy, breakfast buffet had a great selection for many different eating lifestyles. Plenty of seating and lounging areas. Pool was cleaning and hot tub was cozy! ..."

Reviewed on Mar 6, 2025

Homewood Suites Stewart Airport
See all 971 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.