Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Leavenworth Local Hotel
CA $881
per person
Dec 26 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
8.8/10 Excellent! (445 reviews)
Great place to stay. Staff was wonderful. Everything was better than expected. Would absolutely stay here again!
Reviewed on Oct 16, 2026
Margaritaville Hotel Kansas City
I-435 West
CA $1,621
per person
Dec 29 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Kansas City (MCI)
9.2/10 Wonderful! (955 reviews)
The amenities are good pool and restaurant are nice and they have a snack shop. I would of liked a continental breakfast to be included with the price and their was a large stain on the carpeting in the hallway that could of been cleaned the building is less than a year old to look unkept.
Reviewed on Oct 17, 2026
Stoney Creek Hotel Kansas City - Independence
CA $1,035
per person
Dec 26 - Dec 28
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
9.2/10 Wonderful! (2,768 reviews)
One of the most amazing hotels that I have ever stayed at. I booked it based on the reviews and I’m glad I did. The hotel was close to everything in its area and not too far from Kansas City downtown. The breakfast was great. The staff were great! No issues at all. I can’t wait to come back and stay again. My family and I had a great time.
Reviewed on Oct 17, 2026
Crossroads Hotel
Crossroads Arts District
CA $1,899
per person
Dec 29 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Kansas City (MCI)
9.6/10 Exceptional! (1,007 reviews)
They put us on the floor right below the roof and loud music and banging all night and more banging in the morning. I asked for a manager to call me. Also the toilet was making popping sounding most likely due to pressure and splashing water on toilet seat and floor.
Reviewed on Oct 17, 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 $102
CA $111 total
Nov 9 - Nov 10
includes taxes & fees
9.2/10 Wonderful! (111 reviews)
"The room was minimal but clean and functional. The air conditioning worked fabulously. My only issue was the bed was so hard and uncomfortable that it made sleeping difficult but it could just be a matter of prefrence. I do plan on staying again as I can risk a stiff back for the absolute steal of ..."
Reviewed on Oct 12, 2026
Comfort Inn Sedalia Station
3600 W Broadway Blvd Sedalia MO
Fully refundable
CA $162
CA $185 total
Oct 31 - Nov 1
includes taxes & fees
Econo Lodge Truman Inn
3501 W Broadway Blvd Sedalia MO
Fully refundableReserve now, pay when you stay
CA $99
CA $113 total
Oct 26 - Oct 27
includes taxes & fees
5.8/10 (872 reviews)
"Not very clean. Stained sheets and blankets, old towels, you have to put your own app information to watch the TV. Looks like it is long term type place, lots of folks "living" there. Way better choices, I will pass on this next time."
Reviewed on Oct 12, 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 $881 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.
