Deals on vacations and trips to New Windsor

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Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $455, price is now $371 per person
$371
per person
Nov 6 - Nov 9
found 7 hours ago
Roundtrip flight included
Jacksonville (JAX) 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.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Save 100% on your flight
Price was $645, price is now $494 per person
$494
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $4,989, price is now $3,987 per person
$3,987
per person
Dec 4 - Dec 10
just found
Roundtrip flight included
Los Angeles (LAX) to Newburgh (SWF)
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.
Stonehill's Farmhouse

Stonehill's Farmhouse

3.5 out of 5
Price was $617, price is now $498 per person
$498
per person
Nov 21 - Nov 24
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
This bed & breakfast features a restaurant, a sauna, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a garden, and a snack bar/deli are also on offer.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $532, price is now $452 per person
$452
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Newburgh (SWF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

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
$109 nightly
The price is $123 total per night
$123 total
Oct 2 - Oct 3
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

Homewood Suites Stewart Airport

3 out of 5
180 Breunig Rd, New Windsor, NY
$161 nightly
The price is $182 total per night
$182 total
Oct 13 - Oct 14
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

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $115 total per night
$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

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St, Gardiner, NY
$1,260 nightly
The price is $1,411 total per night
$1,411 total
Oct 7 - Oct 8
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

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
$140 nightly
The price is $159 total per night
$159 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.
Pool
Spa
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $139 total per night
$139 total
Oct 1 - Oct 2
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.
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.

Kristi Babcock Memorial Park

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

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.

National Purple Heart Hall of Honor

Frequently asked questions

How much are vacation packages to New Windsor?
$371 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.

Photos of local treasures

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Photo by Wanderlustfemale
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Photo by gavvykins
Photo by gavvykins

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