New Windsor Vacation Packages 2025/2026 from $275

New Windsor flight + hotel vacation packages

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

The Crossroads Hotel, Newburgh

$275

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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.

Sleep Inn & Suites Middletown - Goshen

$291

per person

Feb 6 - Feb 9

found 23 hours ago

Roundtrip non-stop flight included

Houston (HOU) 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.

Courtyard by Marriott Middletown Goshen

$281

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, express check-out, and luggage storage are also on offer.

Hampton Inn & Suites Newburgh Stewart Airport

$401

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Homewood Suites Stewart Airport

$341

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

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.

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

$118 total

per night

Dec 1 - Dec 2

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

$144 total

per night

Dec 7 - Dec 8

The Crossroads Hotel, Newburgh

5 Lakeside Rd, Newburgh, NY

$129 total

per night

Nov 13 - Nov 14

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.

Hampton Inn & Suites Poughkeepsie

2361 South Rd, Poughkeepsie, NY

Free Cancellation

Reserve now, pay when you stay

$115 total

per night

Nov 29 - Nov 30

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-in, and conference space. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

Overlook Lodge at Bear Mountain

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

Free Cancellation

Reserve now, pay when you stay

$118 total

per night

Nov 18 - Nov 19

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.

Windrose On Hudson

1 Shady Lane Farm Road, Ossining, NY

Free Cancellation

Reserve now, pay when you stay

$209 total

per night

Nov 30 - Dec 1

This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and luggage storage are also offered.

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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

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

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?

$275 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.