Windsor Holidays

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Your Windsor Holiday

Uncover the best of Windsor with a customised Windsor holiday package. From its cosmopolitan vibe and diversity to its friendly locals, you'll love experiencing this riverfront city in your own way. You'll want to take in some sights during your trip to Windsor. Find time for big-name attractions such as Detroit Windsor Tunnel, Caesars Casino and Caesars Windsor. Check out Expedia's extensive range of travel options and book your dream holiday to Windsor now.

Our guide on where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Windsor which includes signage

Downtown Windsor

4 out of top 10 points of interest in this area

While visiting Downtown Windsor, you might make a stop by sights like Detroit Windsor Tunnel and Chrysler Theatre.

Find hotels in Downtown Windsor

Windsor Holiday

Windsor Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Windsor Airport (YQG)
Population
278,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Adventure Bay Family Water Park, Chrysler Theatre and Walkerville Brewery

Our pick of the best Windsor Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is AU$221 per night from 1 Sept to 2 Sept
AU$221
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (3,028 reviews)
"Nero’s is overpriced. the food is not chef Ramsey worthy. We would not go back. We were there three different times now and had the same experience. Also they could over a nice baked bread or something like that. But overpriced for the quality and experience."

Reviewed on 7 Aug. 2025

Caesars Windsor
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is AU$218 per night from 12 Aug to 13 Aug
AU$218
12 Aug - 13 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"My husband and I stayed here in July 2025 for a weekend. It was close to the casino and there is also an indoor Waterpark within walking distance. It’s also walking distance to a lot of great restaurants. The room was clean and comfortable."

Reviewed on 5 Aug. 2025

Best Western Plus Waterfront Hotel
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
The price is AU$175 per night from 17 Aug to 18 Aug
AU$175
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,280 reviews)
"Love the buffet breakfast"

Reviewed on 7 Aug. 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 388 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Windsor

Detroit Windsor Tunnel

4/5(1 review)

Find out about the history of Windsor with a stop at Detroit Windsor Tunnel. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Detroit Windsor Tunnel

University of Windsor

Walk around the campus at University of Windsor as part of your travels around Windsor. Amble around this vibrant area's riverfront or experience its entertainment choices.

University of Windsor

Adventure Bay Family Water Park

Bring the children to Adventure Bay Family Water Park and enjoy this exciting theme park in Windsor.

Adventure Bay Family Water Park

What to do in Windsor

Step into the shadows and discover the haunting tales of Motor City's past.

Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

AU$40
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

AU$106
per adult
Roasting Experience at 14th Coffee Co
Detroit: Architectural Beauty and Hidden Gems Walking Tour

Detroit: Architectural Beauty and Hidden Gems Walking Tour

AU$206
per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor holiday 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 holiday to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor holiday package, consider visiting in January, February and April. You'll generally find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Windsor?
To fully enjoy your Windsor holiday, we suggest staying for 2 days. Split your time between discovering Chrysler Theatre, Walkerville Brewery and other well-known attractions, as well as experiencing neighbourhoods like East Windsor and Walkerville. If you've got some time to spare, include a day trip in your Windsor holiday itinerary.
Is it worth booking a holiday package to Windsor?
Windsor offers everything you need for an unforgettable getaway. Get your Windsor holiday off to a flying start by checking out top attractions like Adventure Bay Family Water Park.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you're considering a spontaneous Windsor getaway, 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 awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Windsor?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Windsor.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your accommodation will probably be the largest expense during your trip to Windsor.
  3. Decide how long to go for: Now that you know more about Windsor, you can work out the perfect length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Windsor holiday package that brings all your bookings together.

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