Search Cheap Flights toNew Windsor
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New Windsor Flights as Low as $149
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, May 2 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$149 Roundtrip, found 6 days ago
$149
Roundtrip
found 6 days ago
Fri, May 2 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Fri, May 2 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$211 Roundtrip, found 4 days ago
$211
Roundtrip
found 4 days ago
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$216 Roundtrip, found 4 days ago
$216
Roundtrip
found 4 days ago
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$220 Roundtrip, found 3 days ago
$220
Roundtrip
found 3 days ago
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$221 Roundtrip, found 4 days ago
$221
Roundtrip
found 4 days ago
Fri, Apr 25 - Sun, Apr 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
Fri, Apr 25 - Sun, Apr 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$248 Roundtrip, found 2 days ago
$248
Roundtrip
found 2 days ago
Fri, Apr 11 - Sat, Apr 19
MCO
Orlando Intl.
HPN
Westchester County
$314 Roundtrip, found 5 hours ago
$314
Roundtrip
found 5 hours ago
Tue, Apr 8 - Fri, Apr 18
MCO
Orlando Intl.
HPN
Westchester County
$358 Roundtrip, found 5 hours ago
$358
Roundtrip
found 5 hours ago
Tue, Apr 8 - Fri, Apr 18
MCO
Orlando Intl.
HPN
Westchester County
$358 Roundtrip, found 5 hours ago
$358
Roundtrip
found 5 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 May, 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 $149, 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 $149 right now, why wait?
Destination airport | Stewart Intl. |
Destination airport IATA code | SWF |
Roundtrip price | $148 |
Last Minute Hotel Deals in New Windsor
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave, New Windsor, NY
The price is $123 per night from Apr 6 to Apr 7
$123
includes taxes & fees
Apr 6 - Apr 7
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)
"Very nice stay, friendly staff and clean room. There is a nice balcony on the second floor overlooking a nearby lake. I would definitely stay again."
Reviewed on Mar 25, 2025
Homewood Suites Stewart Airport
180 Breunig Rd, New Windsor, NY
The price is $153 per night from Apr 13 to Apr 14
$153
includes taxes & fees
Apr 13 - Apr 14
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! (990 reviews)
"great"
Reviewed on Mar 31, 2025
Overlook Lodge at Bear Mountain
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is $135 per night from Apr 14 to Apr 15
$135
includes taxes & fees
Apr 14 - Apr 15
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! (1,003 reviews)
"Check in was at a separate building but all went well."
Reviewed on Apr 2, 2025
Sleep Inn & Suites Middletown - Goshen
3491 Route 6, Middletown, NY
The price is $141 per night from Apr 20 to Apr 21
$141
includes taxes & fees
Apr 20 - Apr 21
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 ...
8.6/10 Excellent! (1,006 reviews)
"Best hotel by far in middletown NY Very clean and friendly service."
Reviewed on Apr 3, 2025
La Quinta Inn & Suites by Wyndham Middletown
551 Route 211 E, Middletown, NY
The price is $137 per night from Apr 10 to Apr 11
$137
includes taxes & fees
Apr 10 - Apr 11
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! (665 reviews)
"Excellent property! Everything was neat and clean in the lobby and in the room."
Reviewed on Mar 30, 2025
Hampton Inn Harriman Woodbury
60 Centre Dr, Central Valley, NY
The price is $130 per night from Apr 13 to Apr 14
$130
includes taxes & fees
Apr 13 - Apr 14
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! (1,000 reviews)
"Our “go to” when visiting our cadet at West Point!"
Reviewed on Mar 30, 2025
DoubleTree by Hilton Poughkeepsie
40 Civic Center Plz, Poughkeepsie, NY
The price is $128 per night from Apr 20 to Apr 21
$128
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.2/10 Very Good! (1,000 reviews)
"Very clean and great customer service."
Reviewed on Mar 29, 2025
HYATT house Fishkill/Poughkeepsie
100 Westage Business Center Dr., Fishkill, NY
The price is $124 per night from Apr 6 to Apr 7
$124
includes taxes & fees
Apr 6 - Apr 7
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! (1,003 reviews)
"Enjoyed our stay here. The hotel provided free breakfast, which was scrambled eggs, potatoes, sausage patties or ham and pancakes or french toast depending on the day. Also had a selection of toast and bagel options, cereals, oatmeal and yougurt. The suite also had a kitchenette and there is a walmart ..."
Reviewed on Apr 3, 2025
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
915 Union Ave, New Windsor, NY
The price is $123 per night from Apr 6 to Apr 7
$123
includes taxes & fees
Apr 6 - Apr 7
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)
"Very nice stay, friendly staff and clean room. There is a nice balcony on the second floor overlooking a nearby lake. I would definitely stay again."
Reviewed on Mar 25, 2025
Homewood Suites Stewart Airport
180 Breunig Rd, New Windsor, NY
The price is $153 per night from Apr 13 to Apr 14
$153
includes taxes & fees
Apr 13 - Apr 14
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! (990 reviews)
"great"
Reviewed on Mar 31, 2025
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.
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Top New Windsor Hotels
- Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
- Homewood Suites Stewart Airport
- Overlook Lodge at Bear Mountain
- Sleep Inn & Suites Middletown - Goshen
- Hampton Inn Harriman Woodbury
- HYATT house Fishkill/Poughkeepsie
- Hyatt Place Poughkeepsie / Hudson Valley
- Courtyard by Marriott Middletown Goshen
- Thayer Hotel
- Sleep Inn & Suites Monroe - Woodbury
- Hampton Inn & Suites Newburgh Stewart Airport