Cheap Flights to New Windsor from $52

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How Much Does it Cost To Fly To New Windsor?

The cheapest prices found with in the last 7 days for return flights were $93 and $52 for one-way flights to New Windsor for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Sep 27 - Sun, Sep 28
RSW
Southwest Florida Intl.
HPN
Westchester County
$93 Roundtrip, found 6 days ago
$93
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Sep 27 from Southwest Florida Intl. to Westchester County, returning Sun, Sep 28, priced at $93 found 6 days ago
OriginDestinationTravel DatesFlights From*
FLLWest HarrisonOctober 11 to October 27$97
MCOWest HarrisonNovember 3 to November 4$124
MCONewburghDecember 5 to December 8$147
MIAWest HarrisonSeptember 27 to October 8$160
SJUWest HarrisonOctober 4 to October 5$211
SFOWest HarrisonOctober 11 to October 22$260
LAXWest HarrisonNovember 18 to November 22$263
SFONewburghOctober 2 to October 6$793
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLWest HarrisonSeptember 26 to September 29$117
MIAWest HarrisonSeptember 27 to October 8$160
MCONewburghSeptember 28 to October 3$178
MCOWest HarrisonSeptember 26 to September 28$179
SJUWest HarrisonSeptember 26 to September 30$216
SDQWest HarrisonSeptember 26 to September 30$390
LAXWest HarrisonSeptember 27 to October 6$393
*Prices include taxes and fees

New Windsor Flight Information

Traveling to
New Windsor
Lowest Price
$93
Number of Airlines Serving
Airlines Serving
Breeze Airways, JetBlue Airways
Number of Daily Flights
Airlines with Direct Flights

Flight Review

Dec 14, 2018

Main cabin & “comfort” seats painfully cramped. Had to upgrade (and pay) so I could cross my legs

A verified traveler
Raleigh to New York · Delta
Mar 25, 2018

Great flight attendants on both flights.

A verified traveler
Raleigh to Newark · United

Find The Perfect Hotel For After Your Flight

Amazing New Windsor Accommodation Deals

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
$109 nightly
The price is $123 total per night from Sep 21 to Sep 22
$123 total
Sep 21 - Sep 22
Total with taxes and fees
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)
"Staff was nice, beds comfortable and rooms were clean! Great view of the Lake! Need some benches out there to sit and enjoy the view.No breakfast available Only coffee and juice was available."

Reviewed on Sep 15, 2025

Opens in a new windowRed Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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.

Our Top New Windsor with Airport Shuttles

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
$109 nightly
The price is $123 total per night from Sep 21 to Sep 22
$123 total
Sep 21 - Sep 22
Total with taxes and fees
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)
"Staff was nice, beds comfortable and rooms were clean! Great view of the Lake! Need some benches out there to sit and enjoy the view.No breakfast available Only coffee and juice was available."

Reviewed on Sep 15, 2025

Opens in a new windowRed 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
$179 nightly
The price is $203 total per night from Oct 19 to Oct 20
$203 total
Oct 19 - Oct 20
Total with taxes and fees
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! (1,001 reviews)
"Everything was just fine no issues at all"

Reviewed on Aug 20, 2025

Opens in a new windowHomewood Suites Stewart Airport
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.

Luxury Hotels 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
$109 nightly
The price is $123 total per night from Sep 21 to Sep 22
$123 total
Sep 21 - Sep 22
Total with taxes and fees
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)
"Staff was nice, beds comfortable and rooms were clean! Great view of the Lake! Need some benches out there to sit and enjoy the view.No breakfast available Only coffee and juice was available."

Reviewed on Sep 15, 2025

Opens in a new windowRed Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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.

Family Friendly Hotels in New Windsor

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
The price is $203 total per night from Oct 19 to Oct 20
$203 total
per night
Oct 19 - Oct 20
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! (1,001 reviews)
"Everything was just fine no issues at all"

Reviewed on Aug 20, 2025

Opens in a new windowHomewood Suites Stewart Airport
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 $123 total per night from Sep 21 to Sep 22
$123 total
per night
Sep 21 - Sep 22
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)
"Staff was nice, beds comfortable and rooms were clean! Great view of the Lake! Need some benches out there to sit and enjoy the view.No breakfast available Only coffee and juice was available."

Reviewed on Sep 15, 2025

Opens in a new windowRed Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Countryside Inn & Suites

Countryside Inn & Suites

2 out of 5
310 Windsor Hwy, New Windsor, NY
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions New Windsor Cantonment ...
"Space room was great. I was there for 3 nights I left in second night because there’s a lot noise in the middle of the night"

Reviewed on Nov 28, 2022

Get rates
Opens in a new windowCountryside Inn & Suites
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.

Best New Windsor Flight and Hotel Packages

New Windsor flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $457, price is now $381 per person
$381
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $461, price is now $442 per person
$442
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $482, price is now $464 per person
$464
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Don't see what you're looking for?
See all available trips from Dallas to New Windsor
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Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to New Windsor?
You'll find an impressive range of airlines that fly to New Windsor — 20 to be specific. Popular ones include:

  • United Airlines
  • JetBlue Airways
  • American Airlines

What airport is best to fly into New Windsor?
Decision-making time! There are two airports to select from when jet-setting to New Windsor. Newark Airport is 55 mi from the lively downtown area, while Westchester County Airport (HPN) is around 35 mi away.
Where to stay in New Windsor
Whether you're visiting New Windsor on a family getaway, for work or for an event, we're confident you'll find the ideal place to get some shut-eye. Travelocity offers no less than 101 accommodations within a short distance of the heart of town.Nothing beats the thrill of booking your accommodations for your next trip. But after spending loads of time comparing prices and amenities, it can get a little tedious. So why not take our advice and choose one of our recommended properties, like the Econo Lodge Near Stewart Inter and the Lakefront New Windsor Home w/Sauna & Seasonal Pool?
Places to visit in New Windsor
Enjoy a selection of music shows and artistic events regularly hosted by Storm King Art Center and become more knowledgeable about local culture. Want some more ideas? Browse the exhibits at National Purple Heart Hall of Honor for greater insight into the armed forces. And there's more. Find out what matches are being hosted at Kristi Babcock Memorial Park.
How to get through airport security fast when traveling to New Windsor
Your trip to New Windsor begins as soon as you've finished the security checks. Here are some tips and pointers to make sure you pass through quickly:

  • Keep your passport and boarding pass within easy reach. They'll be the first things you'll be told to produce by airport security personnel.
  • Be aware that metal belt buckles can set off the body scanner's alarms. If you have one on, you may be asked to step back and remove it before moving on.
  • Everyday electronics such as phones, laptops and cameras need to be sent through the X-ray machine separately. Make sure they're within easy reach.
  • When you approach the security checkpoint, you'll be asked to place all gels, liquids and creams in a separate tray for scanning. Make sure they're all packed in containers no larger than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Consider the type of footwear you want to travel in. Slippers are awesome because they're a cinch to remove for the airport security checks. Try wearing some on your next flight!
  • Razors and knives are prohibited from entering the plane. Tuck them away in your checked luggage to avoid them being confiscated at the airport security checkpoint.

Plane Tickets To New Windsor

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to New Windsor. Browse through our inventory to explore a wide range of cheap flights to New Windsor to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in New Windsor as you anxiously await to exit the plane and explore what New Windsor has to offer. Considering all the amazing local food and culture in New Windsor, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to New Windsor to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to New Windsor without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to New Windsor with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to New Windsor today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.