New Windsor Vacation Packages 2026

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

$99 nightly

$117 total

Sep 20 - Sep 21

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.

Pool

Pet friendly

Homewood Suites Stewart Airport

180 Breunig Rd New Windsor NY

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$236 total

Sep 20 - Sep 21

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

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$135 total

Sep 17 - Sep 18

Total with taxes and fees

A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.

Pool

Spa

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Free Cancellation

$110 nightly

$130 total

Oct 13 - Oct 14

Total with taxes and fees

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.

Quality Inn Poughkeepsie

536 Haight Ave, Building A Poughkeepsie NY

$97 nightly

$113 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features an indoor pool and a 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.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E Middletown NY

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$158 total

Sep 20 - Sep 21

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 free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

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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.

Stay near popular New Windsor attractions

New Windsor Cantonment State Historic Site

8.2/10 (12 reviews)

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.

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Frequently asked questions

How much are vacation packages to New Windsor?

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.