Windsor Vacation Packages

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Your Windsor Vacation

When a city stay is calling, answer it with a Windsor vacation package. With all your travel needs in place before you leave, all you have to do here is concentrate on having fun. Every trip to Windsor should include a little sightseeing. le Parc Historique de la Poudriere de Windsor is a superb place to kick off your exploring. Your Windsor vacation is just a few clicks away. Browse airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Masquerade Tower at Rio Hotel & Casino
The LEEF Hotel
Horseshoe Las Vegas
Treasure Island - TI Las Vegas Hotel & Casino
Glendale Hotel

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

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
The price is CA $106 per night from Aug 26 to Aug 27
CA $106
CA $127 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Perfect time with the kiddos"

Reviewed on Jul. 30, 2025

Manoir des Sables Hôtel & Golf
Grand Times Hotel Sherbrooke

Grand Times Hotel Sherbrooke

4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Fully refundable
The price is CA $211 per night from Aug 31 to Sep 1
CA $211
CA $251 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Staff could not let us in 20 minutes before 16:00 checking time. Hotel was not full capacity. Otherwise excellent location"

Reviewed on Jul. 31, 2025

Grand Times Hotel Sherbrooke
Comfort Inn Sherbrooke

Comfort Inn Sherbrooke

2.5 out of 5
4295 boul. Bourque, Sherbrooke, QC
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Aug 17 to Aug 18
CA $127
CA $151 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Large and comfortable King bed. Dining area is small."

Reviewed on Jul. 29, 2025

Comfort Inn Sherbrooke
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.

Discover the most popular places to visit in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $343 on Expedia for your Windsor break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
January, February and November are great times to look for cheap Windsor vacation packages. Choosing to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Windsor?
Typically, a handful of days is enough to visit the major attractions during your Windsor vacation. However, if you prefer to have some time to relax or go on day tours, think about extending your itinerary.
How to find the best Windsor package deals?
Finding a cheap Windsor package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the flexibility to create a customized Windsor vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Windsor?
Enjoy incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor trip.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to visit Windsor.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Windsor.
  3. Decide your trip length: Think about how long you want to spend discovering Windsor. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Windsor vacation package.

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