Windsor Packages (Flight + Hotel)

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Top hotels in Windsor

Grand Times Hotel Sherbrooke
Grand Times Hotel Sherbrooke
4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Fully refundable
8.2/10 Very Good! (1,001 reviews)
"Location near the Lac du Nations, cleanliness, quiet, artwork, everything seemed new."

Reviewed on 5 Jun 2025

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Grand Times Hotel Sherbrooke
Manoir des Sables Hôtel & Golf
Manoir des Sables Hôtel & Golf
4 out of 5
90 Des Jardins Ave., Orford, QC
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,011 reviews)
"Sympathique, comme endroit! Seul commentaire négatif: L'air climatisé faisait un bruit épouvantable lorsqu'il refroidissait l'air ambiant. On aurait dit une alarme qui sonne! Il a fallu remonter la température sur le thermostat pour que le son arrête et qu'il ne fasse que le vrombissement de ..."

Reviewed on 29 Jun 2025

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Manoir des Sables Hôtel & Golf
Hôtel Chéribourg
Hôtel Chéribourg
4 out of 5
2603 Chemin Du Parc, Orford, QC
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,203 reviews)
should be renovated
"It was ok but the place should be renovated"

Reviewed on 25 Jun 2025

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Hôtel Chéribourg
See all 169 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.

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