Windsor Vacation Packages

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    Save 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

Leavenworth Local Hotel

2.5 out of 5
Price was CA $1,044, price is now CA $903 per person
CA $903
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
8.8/10 Excellent! (415 reviews)
Breakfast was an orange or granola bar. Disappointed. The room was great, but not a door on the sleeping area so the TV interfered. Great concept turning a school into a hotel. Large hallways and room.

Reviewed on Jul 19, 2026

Ameristar Casino Hotel Kansas City

Ameristar Casino Hotel Kansas City

4 out of 5
Birmingham Bottoms
Price was CA $1,353, price is now CA $998 per person
CA $998
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
8.6/10 Excellent! (1,147 reviews)

The Inn at Meadowbrook

The Inn at Meadowbrook

4 out of 5
Price was CA $1,243, price is now CA $1,017 per person
CA $1,017
per person
Oct 17 - Oct 19
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9.8/10 Exceptional! (448 reviews)
Everything was just amazing!!

Reviewed on Jun 5, 2026

Origin Kansas City Riverfront, a Wyndham Hotel

Origin Kansas City Riverfront, a Wyndham Hotel

3 out of 5
Price was CA $1,350, price is now CA $1,182 per person
CA $1,182
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
9.6/10 Exceptional! (725 reviews)
Hotel was very clean - was just after Argentina left so the hotel was still had their decor all over, but that was pretty cool. Room was great - except the AC wasn't consistent throughout the entire room, likely because of the rooms shape. Staff were very helpful, especially as it concerned parking. The day I left was the last day of free parking, though their back lot was not available during that time because of the break-down of the facility from Argentina's stay, so perhaps their back lot will remain free parking. All around a great hotel, with access to the tram, riverwalk, and right next to CPKC stadium.

Reviewed on Jul 28, 2026

La Quinta Inn & Suites by Wyndham Kansas City Beacon Hill

La Quinta Inn & Suites by Wyndham Kansas City Beacon Hill

3 out of 5
Beacon Hills
Price was CA $1,298, price is now CA $1,155 per person
CA $1,155
per person
Oct 16 - Oct 19
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
8.8/10 Excellent! (1,709 reviews)

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Windsor Hotel Deals

Windsor Crossroads Motel

Windsor Crossroads Motel

2.5 out of 5
606 North Main Street Windsor MO
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Aug 25 to Aug 26
CA $99
CA $107 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (103 reviews)
"Staff was nice, even though I arrived late. Room was clean and cool."

Reviewed on Jul 25, 2026

Windsor Crossroads Motel
Econo Lodge Truman Inn

Econo Lodge Truman Inn

2 out of 5
3501 W Broadway Blvd Sedalia MO
Fully refundable
The price is CA $110 per night from Aug 2 to Aug 3
CA $110
CA $125 total
Aug 2 - Aug 3
includes taxes & fees
5.8/10 (819 reviews)
"Room was sufficiently clean, staff as ok, parking was available, bed was comfortable. Room needed some updating, Cot that was provided was very uncomfortable. No internet, minimal tv options. Room smelled musty/cigarette like."

Reviewed on Jul 13, 2026

Econo Lodge Truman Inn
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
Get rates
Parkfield Inn
See all 219 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this destination from CA $903 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?

  1. Choose your travel dates: What you want to do in Windsor and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.