New Windsor Vacation Packages 2026 from $265

New Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Sleep Inn & Suites Middletown - Goshen

Save 100% on your flight

$265

per person

Mar 21 - Mar 25

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Buttermilk Falls Inn

$563

per person

Apr 10 - Apr 12

found 5 hours ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Holiday Inn Express Hotel & Suites Chester by IHG

Save 100% on your flight

$362

per person

Mar 21 - Mar 25

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.

Sleep Inn & Suites Monroe - Woodbury

$450

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

This hotel doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

$375

per person

Mar 21 - Mar 25

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Newburgh (SWF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top New Windsor hotels deals

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

915 Union Ave New Windsor NY

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$109 total

Feb 15 - Feb 16

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Free self parking, a computer station, and luggage storage are also offered.

Homewood Suites Stewart Airport

180 Breunig Rd New Windsor NY

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$151 total

Mar 8 - Mar 9

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas, a lobby fireplace, and express check-out are also on offer.

Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$119 total

Feb 19 - Feb 20

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Free Cancellation

$93 nightly

$109 total

Mar 4 - Mar 5

Total with taxes and fees

Hampton Inn Harriman Woodbury

60 Centre Dr Central Valley NY

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$130 total

Feb 19 - Feb 20

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free train station pick-up. Free perks include on-the-go breakfast, free self parking, and a shopping center shuttle.

DoubleTree by Hilton Poughkeepsie Convention Center

40 Civic Center Plz Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$119 total

Feb 21 - Feb 22

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 8 conference rooms, free WiFi in public areas, and express check-out. Free self parking, a coffee shop, and a terrace are also offered.

Don't see what you're looking for?

See all available properties in New Windsor

View all properties

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.

Popular places to visit

National Purple Heart Hall of Honor

5/5(1 review)

You can study the exhibits at National Purple Heart Hall of Honor, a museum with a storied past, during your trip to New Windsor. You can attend a sporting event while in the area.

Knox's Headquarters State Historic Site

4/5(3 reviews)

You can spend an afternoon exploring the galleries in Knox's Headquarters State Historic Site during your travels in New Windsor. Check out the shops and top-notch restaurants in this family-friendly area.

Kristi Babcock Memorial Park

Kristi Babcock Memorial Park is just one of the places to see in New Windsor, so why not enjoy the other things to explore during your travels? You can attend a sporting event while in the area.

Frequently asked questions

How much are vacation packages to New Windsor?

$265 is all you need to spend for a fantastic escape in New Windsor. Bundle your flights and hotel into a Travelocity package and watch the savings add up. With prices as good as these, there's never been a better time to travel.

How long should my New Windsor vacation be?

There are no firm rules when it comes to how long you should spend in New Windsor, but the majority of travelers decide to stay for around 2 nights. Got some flexibility with your travel dates? Extend your trip by a couple of extra nights. Then you'll have enough time to check out the area's off-the-beaten-path gems too.

Where can I get the best vacation package deals for New Windsor?

Look no further than Travelocity. With access to 400 airline partners and a massive 1,000,000 properties worldwide, selecting the ultimate New Windsor package deal couldn't be simpler.

Why should I purchase my New Windsor vacation bundle with Travelocity?

We've got destinations for every type of traveler, first-rate service and 24/7 customer support. On top of that, we'll match any lower price you happen to find with our Price Match Guarantee.

Will I save money on my New Windsor car rental if I book it with hotels and flights?

Combining your hotel, car and flight into a New Windsor vacation package is an excellent way to score an amazing deal. Plus, having your own wheels gives you freedom to find your way to all those big-name sights you're hoping to see. Located 50 mi from New Windsor, Times Square is one attraction that should be on your must-do list. Buckle up and make a day trip of it.

Which airport is best for New Windsor?

John F. Kennedy Intl. Airport (JFK) is 60 mi from downtown and is the beginning point for many adventures. Alternatively, Liberty Intl. Airport (EWR) is 55 mi away from central New Windsor and LaGuardia Airport (LGA) is 50 mi away from central New Windsor.

What is there to do in New Windsor?

You'll feel a certain magic as you stroll the streets of New Windsor. Kristi Babcock Memorial Park and National Purple Heart Hall of Honor are just a couple of attractions that make this city such a sought-after destination, so put them on your must-see list.

Where should I stay when visiting New Windsor?

The Homewood Suites Stewart Airport is the top choice of many visitors. Book soon to avoid missing out.