Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windsor

Manoir des Sables Hôtel & Golf

Manoir des Sables Hôtel & Golf

4 out of 5
90 Des Jardins Ave., Orford, QC
Fully refundable
8.2/10 Very Good! (1,071 reviews)
"Extensive options for activities. Staff pleasant and helpful. Lovely surroundings."

Reviewed on 23 Aug 2025

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Manoir des Sables Hôtel & Golf
Grand Times Hotel Sherbrooke

Grand Times Hotel Sherbrooke

4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Fully refundableReserve now, pay when you stay
The price is 4.271.498 ₫ per night from 31 Aug to 1 Sept
4.271.498 ₫
5.083.044 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"Great location and quiet place"

Reviewed on 21 Aug 2025

Grand Times Hotel Sherbrooke
Comfort Inn Sherbrooke

Comfort Inn Sherbrooke

2.5 out of 5
4295 boul. Bourque, Sherbrooke, QC
The price is 2.243.110 ₫ per night from 14 Sept to 15 Sept
2.243.110 ₫
2.669.281 ₫ total
14 Sept - 15 Sept
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"The personal was very very nice and helpful"

Reviewed on 18 Aug 2025

Comfort Inn Sherbrooke
See all 175 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'll find cheap prices 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.