New Windsor Vacation Packages 2025/2026 from $366

New Windsor flight + hotel vacation packages

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

Howard Johnson by Wyndham Newburgh/West Point

$366

per person

Dec 31 - Jan 3

found 5 hours ago

Roundtrip flight included

Houston (HOU) 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.

The Kartrite Resort & Indoor Waterpark

Save 100% on your flight

$436

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Houston (IAH) 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.

The Crossroads Hotel, Newburgh

$391

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

Houston (HOU) 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.

Caldwell House Bed & Breakfast

$651

per person

Jan 18 - Jan 21

found 2 hours ago

Roundtrip flight included

Houston (HOU) 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.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

$658

per person

Dec 26 - Dec 29

found 8 hours ago

Roundtrip flight included

Memphis (MEM) 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.

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

Oct 26 - Oct 27

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

$138 nightly

$156 total

Nov 23 - Nov 24

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

The Crossroads Hotel, Newburgh

5 Lakeside Rd, Newburgh, NY

$109 nightly

$129 total

Oct 26 - Oct 27

Total with taxes and fees

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.

Parking included

Free WiFi

Hampton Inn & Suites Poughkeepsie

2361 South Rd, Poughkeepsie, NY

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$128 total

Nov 2 - Nov 3

Total with taxes and fees

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.

Breakfast included

Pet friendly

Wildflower Farms, Auberge Collection

2702 Main St, Gardiner, NY

$1,161 nightly

$1,300 total

Nov 25 - Nov 26

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

Quality Inn Poughkeepsie

536 Haight Ave, Building A, Poughkeepsie, NY

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$101 total

Nov 24 - Nov 25

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

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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

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.

Frequently asked questions

How much are vacation packages to New Windsor?

$366 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.