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.
Kansas City Marriott Downtown
Downtown Kansas City
CA $1,362
per person
Nov 5 - Nov 9
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Kansas City (MCI)
9.2/10 Wonderful! (1,122 reviews)
The kindest staff and most professional service. From the bar to the valet and the check-in associates. Real pros.
Reviewed on Aug 24, 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
Aug 26 - Aug 27
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 $124
CA $141 total
Sep 23 - Sep 24
includes taxes & fees
5.8/10 (851 reviews)
"This is probably the worst place we have ever stayed. The staff was unfriendly and reluctant to accommodate us. The AC ran the whole time and barely keep the room cool. The toilet did not flush unless you held the handle down for a minute or two. The shower was out of shampoo and they actually relaced ..."
Reviewed on Aug 24, 2026
Comfort Inn Sedalia Station
3600 W Broadway Blvd Sedalia MO
Fully refundable
CA $159
CA $181 total
Sep 20 - Sep 21
includes taxes & fees
9.2/10 Wonderful! (648 reviews)
"Very clean, staff very friendly and helpful. Great stay over all. One complaint about 9;30 pm people occupying the room above came in and sounded like a heard of horses for an hour stomping around. Will stay again when in that area but will ask for a room on the upper floor."
Reviewed on Aug 23, 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 $1,216 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.
