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 Holiday

Things to do in Windsor

Windsor, Ontario, is an ideal destination for romantic getaways, family holidays, and city excursions. Visitors can enjoy a variety of attractions including educational experiences, vibrant theatre performances, and fun-filled water parks. Additionally, the city offers enticing wedding packages, scenic shore excursions, and engaging day trips, ensuring a memorable stay for all types of travellers.

Shopping

Windsor offers a delightful shopping experience at Devonshire Mall, featuring a variety of shops and entertainment options. If you're up for a drive, consider visiting nearby shopping centres like Tecumseh Mall, which also boasts a range of stores and dining choices.

Recreation

Experience the Chrysler Theatre, where you can enjoy captivating performances that evoke romance and cultural enrichment. For outdoor enthusiasts, the Ambassador Golf Club offers a serene golfing experience amidst lush landscapes, perfect for relaxation and sport. Finally, unwind at Landmark Cinemas Windsor with family-friendly films in a charming setting.

Adventure

Experience the thrills of Adventure Bay Family Water Park, where water slides and wave pools await. For scenic outdoor adventures, explore the Odette Sculpture Park Walking Trail and East Riverside Park Trails, both offering stunning views and a chance to connect with nature on your hiking journey.

Nightlife

Windsor's nightlife is vibrant, centred around the bustling Ouellette Avenue, lined with lively bars, clubs, and lounges. Enjoy live music at local venues, try your luck at the Caesars Windsor Casino, or relax in pubs featuring craft beers and cocktails, offering a warm and welcoming atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Windsor

Windsor offers a delightful blend of romantic and family-friendly experiences, making it an ideal destination for a city-themed getaway. Explore the charming streets, urban parks, and entertainment arenas. Don't miss the iconic Windsor Castle and the picturesque Windsor Bridge, which are perfect for capturing memorable moments. Whether you seek outdoor adventures or cultural attractions, Windsor has something to cater to every traveller's taste.

  • Detroit Windsor Tunnel: Experience the unique atmosphere of this bustling street that connects Windsor and Detroit. The tunnel is not only a vital transport link but also a vibrant thoroughfare where you can feel the city's energy and enjoy the diverse local culture.
  • University of Windsor: Immerse yourself in the rich history and academic ambiance of this esteemed institution. With its beautiful campus and cultural events, the University of Windsor offers a glimpse into the region's educational heritage and community spirit.
  • Ambassador Bridge: As a historic landmark, this iconic bridge serves as a vital connection between Canada and the United States. Stroll along the nearby areas to take in stunning views and appreciate its architectural significance.

Best time to go to Windsor

The best time to visit Windsor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.3°F (-3.7°C)Light RainMostly CloudySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudySlightly LowSlightly Low
March36.3°F (2.4°C)Light RainMostly CloudyAverageSlightly Low
April46.8°F (8.2°C)Light RainMostly SunnySlightly LowAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnyAverageSlightly High
July74.1°F (23.4°C)Light RainMostly SunnySlightly HighAverage
August72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
September66.6°F (19.2°C)Light RainMostly SunnySlightly HighSlightly High
October54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
November41.9°F (5.5°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly CloudyAverageAverage

Tips to save on your trip to Windsor

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor.
  • Consider traveling to Windsor during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

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$134 per night from 9 July to 10 July
AU$134
9 July - 10 July
includes taxes & fees
8.2/10 Very good! (1,073 reviews)
"Great location…wonderful clean room with beautiful views of the river. And such a nice young guy at reception. Yummy cookies when we registered. Parking seemed complicated but was a breeze …just steps from the hotel back entrance."

Reviewed on 6 July 2026

Best Western Plus Waterfront Hotel
Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E Windsor ON
The price is AU$121 per night from 13 July to 14 July
AU$121
13 July - 14 July
includes taxes & fees
8.6/10 Excellent! (3,285 reviews)
"Wonderful! Will stay again!"

Reviewed on 5 July 2026

Caesars Windsor - A Caesars Rewards Destination
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 13 July to 14 July
AU$175
13 July - 14 July
includes taxes & fees
8.8/10 Excellent! (1,407 reviews)
"Check in was a little drawn out because of training. Noted on the reservation, there would be 4 people, but only 3 towels. Room was clean, mattress was comfy. Breakfast was good."

Reviewed on 5 July 2026

Holiday Inn Express Windsor Waterfront by IHG
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.

Stay near popular Windsor attractions

What to do 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.