Windsor Vacation Packages

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Your Windsor Vacation

When a getaway to the city is calling your name, answer it with a Windsor vacation package. With all your travel arrangements under control before you go, all you have to do here is focus on having the time of your life. Fill your trip to Windsor with tours of its big-hitting attractions. First stop? Make a beeline for Wolf Creek State Park. Whoever you're traveling with and whatever your bank balance, your ultimate Windsor vacation is just a few clicks away with Expedia.

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Comfort Suites Mattoon East

Comfort Suites Mattoon East

2.5 out of 5
1408 Broadway Ave E, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Sep 1 to Sep 2
CA $121
CA $136 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (785 reviews)
"Close to several restaurants. Right off hughway."

Reviewed on Aug. 4, 2025

Comfort Suites Mattoon East
Holiday Inn Express & Suites Mattoon by IHG

Holiday Inn Express & Suites Mattoon by IHG

2.5 out of 5
121 Swords Dr, Mattoon, IL
Fully refundable
The price is CA $151 per night from Aug 31 to Sep 1
CA $151
CA $169 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (731 reviews)
"Convenient and friendly. Good complimentary breakfast."

Reviewed on Aug. 2, 2025

Holiday Inn Express & Suites Mattoon by IHG
Suite Dreams Hotel

Suite Dreams Hotel

2.5 out of 5
300 Broadway Avenue East, Mattoon, IL
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Aug 8 to Aug 9
CA $116
CA $130 total
Aug 8 - Aug 9
includes taxes & fees
7.2/10 Good! (492 reviews)
"Perfect location to walk to Bagelfest"

Reviewed on Jul. 20, 2025

Suite Dreams Hotel
See all 69 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'll find cheap prices on Expedia for your Windsor getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation package, consider visiting in January, February and November. You're likely to find better prices on accommodations and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Windsor?
The ideal duration for your Windsor vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to tick off all the top sights and explore some hidden spots along the way.
How to find the best Windsor package deals?
Use Expedia's filter tool to help you find some terrific Windsor package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Windsor package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book 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 flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Windsor vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Windsor?

  1. Pick your dates: What you want to do in Windsor and your favourite season will help you decide when to travel.
  2. Budget wisely: On top of the cost of your stay, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Windsor.
  3. Work out your trip length: Think about how long you want to spend exploring Windsor. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, lock in the right Windsor vacation package for you.

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