New Windsor Vacation Packages

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Flight and hotel packages to New Windsor

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

Cottage Suites

3 out of 5
per person
Jul 18 - Jul 21
Roundtrip flight included
Dayton (DAY) to Newburgh (SWF)
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Top New Windsor hotel deals

Red Roof Inn & Suites Newburgh – Stewart Airport

Red Roof Inn & Suites Newburgh – Stewart Airport

2 out of 5
915 Union Ave, New Windsor, NY
Free Cancellation
Reserve now, pay when you stay
The price is $131 per night
$131
per night
May 5 - May 6
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

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
May 13 - May 14
This hotel features an indoor pool and a 24-hour gym. Enjoy the spa tub and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a free grocery shopping service are also on offer.
Hot Tub
Pet friendly
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
The price is $127 per night
$127
per night
May 7 - May 8
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Pet friendly
Breakfast included
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Free Cancellation
The price is $134 per night
$134
per night
May 5 - May 6
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and free perks like buffet breakfast and free self parking.
Hot Tub
Pet friendly
DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Free Cancellation
Reserve now, pay when you stay
The price is $119 per night
$119
per night
May 28 - May 29
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 8 conference rooms, free WiFi in public areas, and express check-out. Free self parking, a coffee shop, and a terrace are also offered.
Breakfast available
Parking included
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road, Poughkeepsie, NY
Free Cancellation
The price is $103 per night
$103
per night
May 20 - May 21
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pet friendly
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 in New Windsor

Image for Kristi Babcock Memorial Park

Kristi Babcock Memorial Park

Explore the great outdoors at Kristi Babcock Memorial Park, a lovely green space in New Windsor. You can attend a sporting event while in the area.

Kristi Babcock Memorial Park
Image for National Purple Heart Hall of Honor

National Purple Heart Hall of Honor

5/5(1 review)

Rich with history, National Purple Heart Hall of Honor is a cultural attraction worth visiting in New Windsor. You can attend a sporting event while in the area.

National Purple Heart Hall of Honor
Image for New Windsor Cantonment State Historic Site

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.

New Windsor Cantonment State Historic Site

Frequently asked questions

How much are vacation packages to New Windsor?
Travelocity has great package deals to New Windsor, as well as flights and hotels, from an impressive $504. With all that extra cash, you could book some cool tours or perhaps even tack on a few extra nights to your adventure.
How long should my New Windsor vacation be?
Your New Windsor trip can be as short or as long as you want it to be, but many people stay around 2 nights. In the mood to hop off the beaten path and discover some lesser-known sights? Lock in a few more nights and experience another side of this destination.
Where can I get the best vacation package deals for New Windsor?
Your dream escape is waiting for you at Travelocity. With access to 400 airlines and an impressive 1,000,000 worldwide properties, finding the perfect New Windsor package deal couldn’t be simpler.
Why should I purchase my New Windsor vacation bundle via Travelocity?
Because life is one incredible journey, and we’ve got everything you could hope for to get you on your way. With our first-rate service and Price Match Guarantee, you can organize your trip with confidence. Plus, you can sleep easy on the road knowing we’ve got your back with our round-the-clock support.
Can I save money on my New Windsor car rental if I combine it with my hotel or flight?
Combining your car, flight and hotel into a New Windsor vacation package is an easy way to land the best prices. Plus, having your own set of wheels gives you freedom to get to all those big sights you want to see. Located 50 mi from New Windsor, Times Square is one place that should feature on your itinerary. Top up the tank and make a day trip of it.
What is the best time of year to go to New Windsor?
April, May and July is the most popular time to visit, while January, June and December are usually less busy. If your budget is a bit tight, you’d be better off visiting during . is typically the priciest time of the year to stop by.
Which airport is best for New Windsor?
John F. Kennedy Intl. Airport (JFK) is a main hub. You’ll find it roughly 60 mi south of New Windsor. Your other options are Liberty Intl. Airport (EWR) (55 mi away from central New Windsor) and LaGuardia Airport (LGA) (50 mi away from central New Windsor).
What is there to do in New Windsor?
New Windsor has plenty of sights to explore, such as Kristi Babcock Memorial Park and National Purple Heart Hall of Honor. These two popular attractions top most tourists’ travel itineraries.
Where should I stay when visiting New Windsor?
Many visitors stay at the Homewood Suites Stewart Airport. It’s sure to be a good base for your New Windsor vacation.