Windsor Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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

Where to stay in Windsor

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

Things to do in Windsor

Windsor, Ontario, offers a delightful mix of activities perfect for romantic getaways, family holidays, or city explorations. Highlights include the captivating theatre scene and a fantastic water park, alongside the unique attraction of LEGOLAND Windsor. Whether you're seeking an exciting staycation or simply wish to explore this vibrant city, Windsor promises memorable experiences for all visitors.

Shopping

The nearest shopping destination is Devonshire Mall, where you can explore a variety of high street shops, local boutiques, and dining options. If you're up for a drive, consider visiting the nearby Tecumseh Mall for more shopping choices and a vibrant atmosphere.

Recreation

The Chrysler Theatre offers captivating performances, blending romance and culture for an enriching evening. For outdoor enthusiasts, the Ambassador Golf Club provides a serene golfing experience amidst beautiful landscapes. Alternatively, enjoy a film at Landmark Cinemas Windsor, perfect for family outings or a romantic night in.

Adventure

Adventure Bay Family Water Park offers thrilling water slides and fun-filled family activities, perfect for a day of excitement. For nature enthusiasts, Odette Sculpture Park Walking Trail and East Riverside Park Trails provide picturesque hiking routes with stunning scenery, ideal for outdoor adventures and serene exploration.

Nightlife

In Windsor, experience vibrant nightlife at venues like the iconic Caesars Windsor, which offers gaming and live entertainment. Explore the lively bars along Ouellette Avenue, where you can enjoy craft cocktails and live music, creating a lively atmosphere perfect for a memorable night out.

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

Find the best attractions in Windsor

Windsor, Ontario, offers a delightful blend of romantic, city-themed, and family-friendly experiences. Explore popular attractions such as the Windsor Racecourse, Windsor Great Park, Royal Windsor, and the iconic Windsor Castle. With a variety of street and urban parks, as well as entertainment facilities, there's something for everyone seeking outdoor adventures or urban exploration in this charming city.

  • Detroit Windsor Tunnel: Experience the vibrant city atmosphere as you cross this bustling thoroughfare connecting Windsor to Detroit. The tunnel is renowned for its unique urban charm and offers a glimpse into the dynamic life of both cities.
  • Ambassador Bridge: This iconic structure is not only a vital trade link but also a symbol of cultural exchange. Walking along or viewing the bridge provides a profound appreciation of its historical significance and architectural grandeur.
  • University of Windsor: Explore this esteemed institution that boasts a rich history and a vibrant cultural scene. The campus is home to stunning architecture and offers engaging events that reflect the diverse community spirit.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, 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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Windsor.
  • 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.

Top hotels in Windsor

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 €130 per night from 18 Feb to 19 Feb
€130
18 Feb - 19 Feb
includes taxes & fees
8.6/10 Excellent! (3,204 reviews)
Would stay again

Reviewed on 15 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
Fully refundableReserve now, pay when you stay
The price is €76 per night from 22 Feb to 23 Feb
€76
22 Feb - 23 Feb
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
Clean room. Friendly staff.

Reviewed on 10 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
Fully refundable
The price is €112 per night from 27 Feb to 28 Feb
€112
27 Feb - 28 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.

What to do in Windsor

Explore a world of travel with Expedia

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