New Windsor Holidays from AU$3,087

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Your New Windsor Holiday

There's tons to like about New Windsor, from its rich history to its spectacular views and beyond. When you're ready to say hi to this lively city, our New Windsor holiday packages will be right up your alley. Make your trip to New Windsor even more exciting by going sightseeing. Storm King Art Centre, Dia Beacon and Mount Saint Marys College Newburgh are some of the leading attractions worth exploring. Whatever your travel plans or the size of your budget, putting together a tailored New Windsor holiday is a piece of cake with Expedia.

The Latest New Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
13 Apr - 18 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
5.4/10 (1,004 reviews)
Overall, below average but still descent place to stay. Thank you

Reviewed on 23 Feb. 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
13 Apr - 18 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
8.2/10 Very Good! (611 reviews)
Everything great.. except pool area could use upgrade.

Reviewed on 10 Mar. 2025

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

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

2 out of 5
per person
13 Apr - 18 Apr
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
8.4/10 Very Good! (1,005 reviews)
The room was fine, beds were quite comfy. But, the cleaning staff was ridiculously loud very early in the morning, a horn kept beeping all night outside our room, the remote didn’t work, and the pool wasn’t open.

Reviewed on 9 Mar. 2025

New Windsor Holiday

New Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
8,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, Dia Beacon and Brotherhood Winery

Our pick of the best New Windsor Hotel 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
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 12 Mar to 13 Mar
AU$179
includes taxes & fees
12 Mar - 13 Mar
8.2/10 Very Good! (1,000 reviews)
"Best place to stay"

Reviewed on 4 Mar. 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Homewood Suites Stewart Airport
Homewood Suites Stewart Airport
3 out of 5
180 Breunig Rd, New Windsor, NY
Fully refundableReserve now, pay when you stay
The price is AU$213 per night from 17 Mar to 18 Mar
AU$213
includes taxes & fees
17 Mar - 18 Mar
9.2/10 Wonderful! (982 reviews)
Highly recommend and will visit again!
"Wow! From check in to check out we have super friendly staff, the rooms were so clean and aircon/heat worked well. Beds and sofa bed were comfy, breakfast buffet had a great selection for many different eating lifestyles. Plenty of seating and lounging areas. Pool was cleaning and hot tub was cozy! ..."

Reviewed on 6 Mar. 2025

Homewood Suites Stewart Airport
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 17 Mar to 18 Mar
AU$185
includes taxes & fees
17 Mar - 18 Mar
8.6/10 Excellent! (1,017 reviews)
"Awesome"

Reviewed on 8 Mar. 2025

HYATT house Fishkill/Poughkeepsie
See all 980 properties in New Windsor
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a New Windsor holiday package cost?
Offering great value package deals from AU$3,087 on Expedia, you’ll be thrilled with how little a holiday to New Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to New Windsor?
January, February and March are the best times to look for cheap New Windsor holiday packages. Opting to travel in quieter months means you can usually find reduced prices on accommodation and flights.
How many days is enough for New Windsor?
Allow at least 2 days for your New Windsor holiday if you’re hoping to immerse yourself in everything that makes this destination special. Wander around popular areas, including Orange Lake and Vails Gate. Then tick off major sights such as National Purple Heart Hall of Honour and Knox’s Headquarters State Historic Site. With a good itinerary, you can keep busy with room for some rest time too. Want to venture beyond New Windsor? Consider fitting in an excursion or two.
Is it worth booking a holiday package to New Windsor?
New Windsor is a good holiday destination with attractions like National Purple Heart Hall of Honour among the many things to keep you entertained. Whether you’re heading away with the family or planning a trip with friends, a New Windsor holiday promises a good time for everyone.
How to find the best New Windsor package deals?
Use Expedia’s filters to find some fabulous New Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your break for midweek, or browse for New Windsor package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it’s typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a New Windsor holiday as a package?
You can enjoy significant savings on your New Windsor getaway by booking a customised holiday package. Click on the “Package” heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to New Windsor?
If you’re considering a spontaneous New Windsor adventure, check out our last-minute deals that can be booked up to one week before you go. Don’t want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to New Windsor?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit New Windsor.
  2. Budget wisely: As well as the cost of your hotel, you should factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to New Windsor.
  3. Decide how long to go away for: Now that you’re up to speed on New Windsor, you can work out the perfect length of your break. Create a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored New Windsor holiday package.

What to do in New Windsor

7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

AU$1,256
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

AU$217
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

AU$213
per adult
Beacon: Gourmet Beacon Food Tour
See all activities in New Windsor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.