Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $1,346, price is now CA $1,111 per person
CA $1,111
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Kansas City (MCI)
8.8/10 Excellent! (404 reviews)
What a unique place. An old Catholic school converted into a hotel. Even had a basketball court! The room was spacious and had the original school blackboard on the wall with chalk! 😂 The only thing to keep in mind - no elevator. So request 1st floor if you have heavy luggage. Staff (James) was awesome. Will absolutely stay again if I’m in the area!!

Reviewed on Jul 13, 2026

Ameristar Casino Hotel Kansas City

Ameristar Casino Hotel Kansas City

4 out of 5
Birmingham Bottoms
Price was CA $1,740, price is now CA $1,112 per person
CA $1,112
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
8.6/10 Excellent! (1,129 reviews)
Great stay!

Reviewed on Jul 13, 2026

The Elms Hotel & Spa, a Destination by Hyatt Hotel

The Elms Hotel & Spa, a Destination by Hyatt Hotel

4 out of 5
Price was CA $1,738, price is now CA $1,377 per person
CA $1,377
per person
Aug 19 - Aug 23
found 18 hours ago
Roundtrip flight included
Halifax (YHZ) to Kansas City (MCI)
8.8/10 Excellent! (1,006 reviews)
Very nice

Reviewed on Jul 13, 2026

AC Hotel Lenexa City Center

AC Hotel Lenexa City Center

3 out of 5
Lenexa City Center
Price was CA $1,873, price is now CA $1,529 per person
CA $1,529
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kansas City (MCI)
No reviews

The Fontaine

The Fontaine

4.5 out of 5
West Plaza
Price was CA $1,905, price is now CA $1,569 per person
CA $1,569
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Kansas City (MCI)
9/10 Wonderful! (1,006 reviews)
Great location, nice lobby, decent rooms. Staff is helpful but found them often busy talking to each other and leaving guests waiting - experienced this at the front desk and the pool deck. A/C in the room is not subtle and blows directly onto the bed.

Reviewed on Jul 13, 2026

Ready to book your vacation to Windsor?

 

Choose your dates

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 17 to Jul 18
CA $99
CA $108 total
Jul 17 - Jul 18
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
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
The price is CA $132 per night from Aug 3 to Aug 4
CA $132
CA $149 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"The hotel was very clean and you could tell the entire staff was on board to keep it that way. Across the board every area of the hotel was very clean. We will definitely stay at the property again. The only sub par aspect was the breakfast, but that will not keep us from choosing to stay our next ..."

Reviewed on Jul 13, 2026

Parkfield Inn
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 Jul 16 to Jul 17
CA $110
CA $125 total
Jul 16 - Jul 17
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
See all 213 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this destination from CA $1,111 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.