New Windsor Vacation Packages 2025/2026 from $355

New Windsor flight + hotel vacation packages

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

Sleep Inn & Suites Middletown - Goshen

$355

per person

Nov 5 - Nov 9

found 10 hours ago

Roundtrip 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.

YO1 Longevity & Health Resorts, Catskills

Save 100% on your flight

$611

per person

Oct 31 - Nov 3

found 1 hour ago

Roundtrip flight included

Miami (MIA) to Newburgh (SWF)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.

The Kartrite Resort & Indoor Waterpark

Save 100% on your flight

$403

per person

Oct 31 - Nov 3

found 1 hour ago

Roundtrip flight included

Miami (MIA) to Newburgh (SWF)

A water park, 5 restaurants, and an outdoor pool are all featured at this smoke-free hotel. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Save 100% on your flight

$466

per person

Nov 5 - Nov 9

found 10 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 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Hampton Inn by Hilton Middletown

$386

per person

Nov 5 - Nov 9

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to Newburgh (SWF)

This hotel features a gym and a seasonal outdoor pool. 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.

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

$109 nightly

$123 total

Sep 30 - Oct 1

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

$161 nightly

$182 total

Oct 26 - Oct 27

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

Quality Inn Poughkeepsie

536 Haight Ave, Building A, Poughkeepsie, NY

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$115 total

Oct 28 - Oct 29

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.

Pool

Breakfast included

Wildflower Farms, Auberge Collection

2702 Main St, Gardiner, NY

$1,211 nightly

$1,356 total

Sep 30 - Oct 1

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

Pool

Spa

Overlook Lodge at Bear Mountain

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

$147 nightly

$167 total

Oct 7 - Oct 8

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.

Sleep Inn & Suites Middletown - Goshen

3491 Route 6, Middletown, NY

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$123 total

Sep 30 - Oct 1

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.

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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?

$355 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.