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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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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 $1,005, price is now CA $842 per person
CA $842
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
8.8/10 Excellent! (404 reviews)
Wonderfully unique experience. Helpful folks. Perfect.

Reviewed on Jul 7, 2026

Home2 Suites by Hilton Overland Park

Home2 Suites by Hilton Overland Park

3 out of 5
Price was CA $954, price is now CA $862 per person
CA $862
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
8.6/10 Excellent! (703 reviews)
The staff, Kai and Katie were extremely friendly and helpful! The property was well maintained and very clean. Our room was clean, spacious and nicely appointed. Laundry facility worked out perfect and the pool was refreshing!! Great place to stay.

Reviewed on Jul 1, 2026

SpringHill Suites by Marriott Kansas City Lenexa City Center

SpringHill Suites by Marriott Kansas City Lenexa City Center

3 out of 5
Lenexa City Center
Price was CA $1,240, price is now CA $1,136 per person
CA $1,136
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9/10 Wonderful! (526 reviews)
Staff members were always very helpful. Hotel and our room were clean.

Reviewed on Jul 6, 2026

SpringHill Suites by Marriott Overland Park Leawood

SpringHill Suites by Marriott Overland Park Leawood

2.5 out of 5
Price was CA $1,118, price is now CA $1,036 per person
CA $1,036
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9.2/10 Wonderful! (675 reviews)
I did like the location it was very convenient for me

Reviewed on Jul 5, 2026

Candlewood Suites Lenexa - Overland Park Area by IHG

Candlewood Suites Lenexa - Overland Park Area by IHG

2.5 out of 5
Price was CA $977, price is now CA $915 per person
CA $915
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kansas City (MCI)
9.2/10 Wonderful! (570 reviews)
Utilitarian but perfectly fine.

Reviewed on Jun 26, 2026

Ready to book your vacation to Windsor?

 

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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 Jul 10 to Jul 11
CA $99
CA $108 total
Jul 10 - Jul 11
includes taxes & fees
9/10 Wonderful! (101 reviews)
"I don’t have enough good things to say about this property. The rooms are very well cleaned and adequately maintained, despite it being an older property. The exterior is super cute and there are accommodating areas to gather, including a fire pit. It’s very quiet. The best thing about it is the ..."

Reviewed on May 31, 2026

Windsor Crossroads Motel
Econo Lodge Truman Inn

Econo Lodge Truman Inn

2 out of 5
3501 W Broadway Blvd Sedalia MO
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Jul 9 to Jul 10
CA $116
CA $132 total
Jul 9 - Jul 10
includes taxes & fees
5.8/10 (818 reviews)
"We always stay there when we are in Sedalia!! Rooms are clean...the staff is very nice and helpful and it's so close to shopping! We have never had an issue yet!! Thank you so much and we will be back!!!"

Reviewed on Jul 5, 2026

Econo Lodge Truman Inn
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Jul 13 to Jul 14
CA $138
CA $156 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Nice pool. Staff was confused and the room had a really bad smell. They said they had been using acetone to clean the rooms. We both woke with headache. Washed our clothes and dryer was down. We where refunded our money and they put an out of service sign on it. Saw front desk remove it sign."

Reviewed on Jul 5, 2026

Parkfield Inn
See all 216 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.
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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 $842 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.

Explore a world of travel with Expedia

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