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.

The Annual Holiday Sale

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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

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$206 per night from 8 Mar to 9 Mar
AU$206
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (3,200 reviews)
Room was great, really nice review

Reviewed on 20 Feb 2026

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

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West Windsor ON
The price is AU$128 per night from 22 Feb to 23 Feb
AU$128
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
Very nice place Beautiful View

Reviewed on 19 Feb 2026

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
The price is AU$177 per night from 24 Feb to 25 Feb
AU$177
24 Feb - 25 Feb
includes taxes & fees
8.6/10 Excellent! (1,380 reviews)
Very clean, clean and modern building

Reviewed on 8 Feb 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.

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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.