Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Fontaine
West Plaza
CA $1,192
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9/10 Wonderful! (1,069 reviews)
A great long weekend stay for a family wedding. The on- site bar and cafe are wonderfully charming, and the staff really attentive and helpful overall. We loved our stay and the location/ walkability of the area. Let’s not forget the plush bedding and soft sheets ensuring a good night’s rest. Thank you!
Reviewed on Sep 7, 2026
Origin Kansas City Riverfront, a Wyndham Hotel
CA $1,116
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9.6/10 Exceptional! (795 reviews)
Based on reviews, I was expecting something really special. Instead, we experienced very thin walls, a weird parking situation that required phon
Reviewed on Sep 8, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Windsor Crossroads Motel
606 North Main Street Windsor MO
Fully refundableReserve now, pay when you stay
CA $96
CA $105 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (109 reviews)
"Great place to stay. Friendly and professional staff. Clean rooms."
Reviewed on Aug 24, 2026
Econo Lodge Truman Inn
3501 W Broadway Blvd Sedalia MO
CA $113
CA $129 total
Sep 22 - Sep 23
includes taxes & fees
Westbridge Inn and Suites
106 S Baird St. Clinton MO
Fully refundableReserve now, pay when you stay
CA $110
CA $129 total
Sep 21 - Sep 22
includes taxes & fees
8/10 Very good! (835 reviews)
"Room was in bad need of a deep cleaning. Carpet was dirty, the back of the bathroom door was filthy, and there was a ton of dust along the baseboards. Definitely would not stay here again."
Reviewed on Sep 6, 2026
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 vacation package cost?
You can pick up a vacation package to this destination from CA $1,046 on Expedia. But how much your vacation to Windsor costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Windsor?
January, March and October are the best times to look for cheap Windsor vacation packages. Opting to travel in quieter months means you'll typically find better prices on flights and hotels.
How many days is enough for Windsor?
With a well-organized travel plan, you can easily tick off the top Windsor sights in a handful of days. But if you want to venture off the beaten track or go on day trips, consider booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Use Expedia's filters to find some terrific Windsor package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Windsor package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Windsor vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Windsor?
If you're considering a spontaneous Windsor getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Windsor?
- Choose your travel dates: What you want to do in Windsor and your preferred season can help you decide when to go.
- Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Windsor.
- Decide how many days away: Start by making a list of all the attractions you'd like to experience in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Windsor vacation 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.
