New Windsor Vacation Packages 2025/2026 from $321

New Windsor flight + hotel vacation packages

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

The Crossroads Hotel, Newburgh

per person

Sep 20 - Sep 24

found 2 hours ago

Roundtrip flight included

Denver (DEN) to Newburgh (SWF)

A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.

Courtyard by Marriott Newburgh Stewart Airport

per person

Aug 31 - Sep 6

found 24 hours ago

Roundtrip non-stop flight included

Denver (DEN) 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.

Howard Johnson by Wyndham Newburgh/West Point

per person

Sep 6 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

Tulsa (TUL) to Newburgh (SWF)

This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

per person

Sep 6 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

Tulsa (TUL) to Newburgh (SWF)

This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box is provided and the front desk is staffed around-the-clock.

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

per person

Sep 20 - Sep 24

found 2 hours ago

Roundtrip flight included

Denver (DEN) 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

$119 nightly

$135 total

Jul 27 - Jul 28

Total includes 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

$178 nightly

$201 total

Aug 3 - Aug 4

Total includes 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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$130 total

Aug 3 - Aug 4

Total includes 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 continental breakfast and free self parking.

Pool

Breakfast included

Overlook Lodge at Bear Mountain

55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$136 total

Aug 26 - Aug 27

Total includes 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

Reserve now, pay when you stay

$104 nightly

$123 total

Aug 10 - Aug 11

Total includes 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.

Pool

Breakfast included

Hampton Inn Harriman Woodbury

60 Centre Dr, Central Valley, NY

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$156 total

Aug 3 - Aug 4

Total includes 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.

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.

Popular places to visit

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.

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.

National Purple Heart Hall of Honor

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.

Frequently asked questions

How much are vacation packages to New Windsor?

$321 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.