Windsor Holidays from NZ$3,881

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The Latest Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was NZ$5,387, price is now NZ$3,881 per person
NZ$3,881
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
No fan in bathroom

Reviewed on 17 July 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was NZ$7,397, price is now NZ$4,807 per person
NZ$4,807
per person
29 Aug - 5 Sept
found 13 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
It may have been because of FIFA…in the mornings trying to go down for breakfast was a struggle…the elevators were packed and we had to let several (3-4) go by before finally pushing onto the elevator. The guests were just as polite as the staff…everyone understood.

Reviewed on 17 July 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was NZ$6,419, price is now NZ$4,332 per person
NZ$4,332
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9.2/10 Wonderful! (3,746 reviews)
We had a beautiful view of the city and the iconic New Years Eve ball. The bed was very comfortable and breakfast was delicious. Will definitely stay here again.

Reviewed on 17 July 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was NZ$6,270, price is now NZ$4,246 per person
NZ$4,246
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
This hotel is adorable. Great location. Rooms are a great size. We will be back!

Reviewed on 17 July 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was NZ$7,095, price is now NZ$4,943 per person
NZ$4,943
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
Loved the front desk staff and the bell staff. Hated that I was charged $210 for parking when I didn’t even have a car there. Still waiting to be refunded. They said they need to investigate. Smh.

Reviewed on 17 July 2026

Windsor Holiday

Our pick of the best Windsor Hotel Deals

Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
The price is NZ$298 per night from 16 Aug to 17 Aug
NZ$298
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (1,328 reviews)
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Reviewed on 16 July 2026

Hyatt Regency Princeton
Hilton East Brunswick Hotel & Executive Meeting Center

Hilton East Brunswick Hotel & Executive Meeting Center

3.5 out of 5
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
The price is NZ$232 per night from 22 July to 23 July
NZ$232
22 July - 23 July
includes taxes & fees
7.4/10 Good! (1,165 reviews)
"Room had hair in the tub upon arrival. The ac unit was broken, and when we got it fixed by maintenance (which did arrive quickly) the ac unit then leaked water all over the floor the next morning and got on some of our luggage. The outside and the lobby are very pretty! The rooms are old and outdated ..."

Reviewed on 17 July 2026

Hilton East Brunswick Hotel & Executive Meeting Center
Radisson Hotel Freehold

Radisson Hotel Freehold

3.5 out of 5
50 Gibson Pl Freehold NJ
Fully refundable
The price is NZ$300 per night from 10 Aug to 11 Aug
NZ$300
10 Aug - 11 Aug
includes taxes & fees
Radisson Hotel Freehold
See all 429 properties in 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.

Frequently asked questions

How much does a Windsor holiday package cost?
You can snap up a holiday package to this top destination from NZ$3,881 on Expedia. But how much your holiday to Windsor costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor?
January, February and March are the best times to look for cheap Windsor holiday packages. Opting to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Windsor?
Typically, a handful of days is enough to explore the main sights during your Windsor holiday. But if you prefer to have some time to relax or go on day trips, think about extending your itinerary.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Windsor package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalise your Windsor escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Windsor?
If you have your Windsor travel dates locked in, book as early as you can to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Windsor?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Windsor.
  2. Set your budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to Windsor. Then, pick a property that fits your budget, whether that's an economical stay or a more luxurious getaway.
  3. Decide your trip length: Consider how long you'd like to spend exploring Windsor. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Windsor holiday package.

Explore a world of travel with Expedia

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