Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windsor

Manoir Des Sables, an Ascend Collection Hotel

Manoir Des Sables, an Ascend Collection Hotel

4 out of 5
90 Des Jardins Ave. Orford QC
Fully refundable
The price is 2.266.977 ₫ per night from 5 Jul to 6 Jul
2.266.977 ₫
2.857.322 ₫ total
5 Jul - 6 Jul
includes taxes & fees
8.4/10 Very good! (1,318 reviews)
"All good"

Reviewed on 2 Jul 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 refundable
The price is 2.151.758 ₫ per night from 8 Jul to 9 Jul
2.151.758 ₫
2.720.518 ₫ total
8 Jul - 9 Jul
includes taxes & fees
8.2/10 Very good! (1,219 reviews)
"Oui"

Reviewed on 2 Jul 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 2.535.405 ₫ per night from 19 Jul to 20 Jul
2.535.405 ₫
3.017.110 ₫ total
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Staff were great! Rooms were clean and the air was on which was great since there was a heat warning! Very thoughtful!"

Reviewed on 2 Jul 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.
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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.

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