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New Windsor flight + hotel packages

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Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Jan. 5 - Jan. 9
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
per person
Jan. 5 - Jan. 9
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

2 out of 5
per person
Jan. 5 - Jan. 9
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Columbus Hotel

Columbus Hotel

3 out of 5
per person
Jan. 5 - Jan. 9
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
Stay at this 3-star B&B in Middletown. Enjoy free WiFi, free parking, and bathrobes. Popular attractions Paramount Theatre and Orange County Fair Speedway are located nearby.

Top New Windsor hotels deals

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

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

2 out of 5
915 Union Ave, New Windsor, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $168 total
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Pool
Pet-friendly
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 CA $189 per night
CA $189
CA $214 total
includes taxes & fees
3 Dec - 4 Dec
Stay at this 3-star hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hamilton Fish Bridge and National Purple Heart Hall of Honor are located nearby.
Pool
Hot tub
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $188 total
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
Pool
Spa
Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

3.5 out of 5
14 Schuyler Blvd, Fishkill, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $145 total
includes taxes & fees
5 Dec - 6 Dec
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Van Wyck Homestead Museum and Blodgett Memorial Library are located nearby.
Pool
Breakfast included
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 CA $147 per night
CA $147
CA $171 total
includes taxes & fees
5 Dec - 6 Dec
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions McCann Ice Arena and Mid-Hudson Civic Center are located nearby.
Parking included
Free WiFi
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
CA $175 total
includes taxes & fees
3 Dec - 4 Dec
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course are located nearby.
Pool
Hot tub
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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

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

National Purple Heart Hall of Honor

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

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.

Knox's Headquarters State Historic Site

New Windsor Vacations

It's always a wise idea to learn a thing or two about your destination before you rush off on your travels. Circle New Windsor on your map now and start packing your bags for your next great adventure!

New Windsor is a neighborhood in Newburgh. You'll find it 4 miles (6 kilometers) southwest of the downtown area.

Ready to meet some of the locals? 29,000 people reside in Newburgh.

Places to visit in New Windsor

Be sure to get on your most avant-garde outfit before heading to Storm King Art Center. Putting on a variety of festivals, performances and exhibits throughout the year, it's a major part of the cultural landscape. Want some more nearby options? You don't have to be a prodigy to admire the vast lecture halls and intriguing stories of New York Military Academy. But that's not all. The world as we know it has been indelibly marked by war. Visit National Purple Heart Hall of Honor to learn more about the great battles of the past.

Where do you fly into for New Windsor?

Flying into LaGuardia Airport (LGA)? New Windsor is 50 miles (80 kilometers) from here. Grab a cup of coffee, wave down a cab and you'll be there in no time!

Frequently asked questions

How much are vacation packages to New Windsor?
CA $584 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 80 kilometers 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 97 kilometers from downtown and is the beginning point for many adventures. Alternatively, Liberty Intl. Airport (EWR) is 88 kilometers away from central New Windsor and LaGuardia Airport (LGA) is 80 kilometers 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.

Photos of local treasures

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Photo by Wanderlustfemale
Photo by Wanderlustfemale
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Photo by gavvykins