Windsor Holidays from NZ$3,356

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The Latest Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Short Stories Hotel

Short Stories Hotel

4 out of 5
Beverly Grove
Price was NZ$4,526, price is now NZ$3,356 per person
NZ$3,356
per person
19 Aug - 25 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
9.2/10 Wonderful! (1,004 reviews)
The front staff seemed like we bothered them with our checking in, but the room was nice and the location was central.

Reviewed on 30 June 2026

Sofitel New York

Sofitel New York

4.5 out of 5
Manhattan
Price was NZ$5,922, price is now NZ$4,176 per person
NZ$4,176
per person
17 Aug - 23 Aug
found 3 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (1,243 reviews)
Room was clean, staff were extremely helpful, valet was easily accessible.

Reviewed on 30 June 2026

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was NZ$4,927, price is now NZ$3,592 per person
NZ$3,592
per person
17 Aug - 23 Aug
found 3 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (1,828 reviews)
Great hotel with helpfully staff and clean rooms. Great location within walking distance to Rockefeller Plaza, Radio City Music Times Square, Grand Central Station, and Broadway. About 1/2 to 1 mile. Near many restaurants and several subway stations. Great value.

Reviewed on 30 June 2026

New York Downtown Stay

New York Downtown Stay

2 out of 5
Manhattan
Save 100% on your flight
Price was NZ$24,146, price is now NZ$18,326 per person
NZ$18,326
per person
17 Aug - 23 Aug
found 3 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
No reviews

Fairmont Miramar Hotel

Fairmont Miramar Hotel

5 out of 5
Wilshire Montana
Price was NZ$5,894, price is now NZ$4,501 per person
NZ$4,501
per person
19 Aug - 25 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Los Angeles (LAX)
8.6/10 Excellent! (1,004 reviews)
Amazing location, beautiful views of the ocean, plenty of green landscape m, trees, and relaxation spots for winding down. Excellent food located on property, and staff were all friendly and helpful. The bathroom could use an update, but the positive ls far outweigh the bathroom decor. We will be back at the Fairmont SM.

Reviewed on 25 June 2026

Windsor Holiday

Our pick of the best Windsor Hotel Deals

Manoir Des Sables, an Ascend Collection Hotel

Manoir Des Sables, an Ascend Collection Hotel

4 out of 5
90 Des Jardins Ave. Orford QC
The price is NZ$180 per night from 27 July to 28 July
NZ$180
27 July - 28 July
includes taxes & fees
8.4/10 Very good! (1,314 reviews)
"We had a wonderful stay at Manoir des Sables. The staff were friendly and welcoming, the room was clean and comfortable, and the hotel grounds were beautiful and well maintained. The location is perfect for exploring Magog and Orford, while still being peaceful and relaxing. We especially enjoyed ..."

Reviewed on 30 June 2026

Manoir Des Sables, an Ascend Collection Hotel
Hotel Cheribourg, an Ascend Collection Hotel

Hotel Cheribourg, an Ascend Collection Hotel

4 out of 5
2603 Chemin Du Parc Orford QC
Fully refundableReserve now, pay when you stay
The price is NZ$163 per night from 2 July to 3 July
NZ$163
2 July - 3 July
includes taxes & fees
8.2/10 Very good! (1,217 reviews)
"Great place to stay while visiting the area. So much to do around Orford, Magog and other towns close by. Hotel itself was clean and quiet. It does need some TLC on the outside but did not disappoint. The kids playroom room was an awesome addition your kids will love it."

Reviewed on 30 June 2026

Hotel Cheribourg, an Ascend Collection Hotel
Comfort Inn Sherbrooke - Estrie

Comfort Inn Sherbrooke - Estrie

2.5 out of 5
4295 boul. Bourque Sherbrooke QC
Fully refundableReserve now, pay when you stay
The price is NZ$198 per night from 12 July to 13 July
NZ$198
12 July - 13 July
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Breakfast was good with bacon, sausage ,scrabbles egg etc... However breakfast area is small. The staff was very good."

Reviewed on 30 June 2026

Comfort Inn Sherbrooke - Estrie
See all 188 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.

Stay near popular Windsor attractions

le Parc Historique de la Poudriere de Windsor

Find out about the history of Windsor with a stop at le Parc Historique de la Poudriere de Windsor. You can enjoy the restaurants while in the area.
See properties

Frequently asked questions

How much does a Windsor holiday package cost?
You'll find cheap prices from NZ$3,356 on Expedia for your Windsor getaway. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
January, February and November are the best times to look for cheap Windsor holiday packages. Opting to travel in less busy periods means you can typically find better prices on accommodation and flights.
How many days is enough for Windsor?
Generally, a handful of days is enough to visit the main sights during your Windsor holiday. However, if you want to have more time to relax or go on day tours, think about extending your itinerary.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Windsor package deal straight away, just change your dates and search again. Keep in mind 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?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you're planning a spontaneous Windsor holiday, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Windsor?

  1. Choose your travel dates: The things you plan to do in Windsor and your preferred season can help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Windsor.
  3. Decide how long to go for: Now that you're up to speed on Windsor, you can figure out the ideal length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Windsor holiday package that brings all your bookings together.

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