New Windsor Holidays from NZ$11,441

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The Latest New Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
per person
19 Sept - 23 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Newburgh (SWF)
9.6/10 Exceptional! (51 reviews)
Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch

Reviewed on 15 May 2025

New Windsor Holiday

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 NZ$224 per night from 17 July to 18 July
NZ$224
17 July - 18 July
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Our stay was very pleasant. The staff was super kind and helpful. Our room was also clean, and overall, I Our stay was very beautiful view was perfect for the nights day that I had with me and my family. Are only concern was it did mention there would be breakfast provided. And there wasn’t. They ..."

Reviewed on 7 Jul. 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 NZ$314 per night from 20 July to 21 July
NZ$314
20 July - 21 July
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Staff was great. Easy if traveling to or from teh airport"

Reviewed on 8 Jul. 2025

Homewood Suites Stewart Airport
La Quinta Inn & Suites by Wyndham Middletown-Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
3 out of 5
551 Route 211 E, Middletown, NY
The price is NZ$221 per night from 28 July to 29 July
NZ$221
28 July - 29 July
includes taxes & fees
9.2/10 Wonderful! (746 reviews)
"I loved this hotel!!! The staff, the hotel itself, the location, everything. We will for sure stay here again"

Reviewed on 11 Jul. 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 1,003 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.

What to do in New Windsor

BEST Woodbury Outlets Shopping 1-Day Tour from New York

Woodbury Outlets Shopping 1-Day Tour from New York-Kids 50 Percent Off

NZ$103
per adult
Woodbury Outlets Shopping 1-Day Tour from New York-Kids 50 Percent Off
Woodbury Common Premium Outlets Shopping Tour from Midtown

Woodbury Common Premium Outlets Shopping Tour from Midtown

NZ$78
per adult
96% of travellers recommend
Woodbury Common Premium Outlets Shopping Tour from Midtown
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

NZ$221
per adult
Beacon: Gourmet Beacon Food Tour
See all activities in New Windsor

Frequently asked questions

How much does a New Windsor holiday package cost?
Offering great value package deals from NZ$11,441 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.