New Windsor Vacation Packages 2026 from $312

New Windsor flight + hotel vacation packages

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

Courtyard by Marriott Newburgh Stewart Airport

$312

per person

May 8 - May 10

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Newburgh (SWF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Sleep Inn & Suites Middletown - Goshen

$482

per person

May 23 - May 25

found 11 hours ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Caldwell House Bed & Breakfast

$907

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Free full breakfast is served. A garden, a lobby fireplace, and a library are also on offer.

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

$394

per person

Apr 3 - Apr 7

found 24 hours ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

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.

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

Mar 1 - Mar 2

Total with taxes and fees

Homewood Suites Stewart Airport

180 Breunig Rd New Windsor NY

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$149 total

Mar 22 - Mar 23

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.

Pool

Hot Tub

Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$119 total

Mar 19 - Mar 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

$103 nightly

$122 total

Mar 8 - Mar 9

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

Mar 8 - Mar 9

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.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E Middletown NY

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$142 total

Mar 5 - Mar 6

Total with taxes and fees

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.

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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.

New Windsor Cantonment State Historic Site

You can find out about the history of New Windsor with a stop at New Windsor Cantonment State Historic Site. 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.

Frequently asked questions

How much are vacation packages to New Windsor?

$312 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.