Title: Windsor Vacation Packages & Trips 2026  | Expedia.ca

[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d175567.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d175567.Travel-Guide-VacationRentals)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d175567.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windsor Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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

#### 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](https://www.expedia.ca/Wolf-Creek-State-Park-Illinois.d553248621561881810.Vacation-Attraction). 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](https://images.trvl-media.com/lodging/1000000/480000/474300/474235/6759fc3e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Comfort Suites Mattoon East

1408 Broadway Ave E Mattoon IL

Fully refundableReserve now, pay when you stay

CA $113

CA $127 total

Jan 11 - Jan 12

includes taxes & fees

8.6/10 Excellent! (884 reviews)

Clean rooms, friendly staff, and great breakfast.

Reviewed on Dec 29, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=474235&PinnedHotelID=474235&HadPinnedHotel=true&regionId=175567)

![Hilton Garden Inn Mattoon,  Il](https://images.trvl-media.com/lodging/79000000/78290000/78285200/78285150/12c48720_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Garden Inn Mattoon, Il

100 Coles Centre Parkway Mattoon IL

Fully refundableReserve now, pay when you stay

CA $179

CA $199 total

Jan 11 - Jan 12

includes taxes & fees

8.8/10 Excellent! (211 reviews)

Quick check-in and good room.

Reviewed on Dec 23, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=78285150&PinnedHotelID=78285150&HadPinnedHotel=true&regionId=175567)

![Holiday Inn Express & Suites Mattoon by IHG](https://images.trvl-media.com/lodging/2000000/1860000/1850700/1850633/c6bf8414_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Express & Suites Mattoon by IHG

121 Swords Dr Mattoon IL

Fully refundable

CA $128

CA $143 total

Jan 11 - Jan 12

includes taxes & fees

8.2/10 Very Good! (752 reviews)

Great 👍

Reviewed on Dec 29, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=1850633&PinnedHotelID=1850633&HadPinnedHotel=true&regionId=175567)

[See all 73 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&regionId=175567)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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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.

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