Windsor Holidays

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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

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 €82 per night from 7 Jul to 8 Jul
€82
7 Jul - 8 Jul
includes taxes & fees
8.2/10 Very good! (1,058 reviews)
"Nice hotel. Stayed many times before."

Reviewed on 30 Jun 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 €74 per night from 13 Jul to 14 Jul
€74
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (3,267 reviews)
"Everything Was all in one place parking restaurants, casino especially for elderly who have difficulty with walking. Staff was very friendly and helpful, and made our weekend getaway special."

Reviewed on 1 Jul 2026

Caesars Windsor - A Caesars Rewards Destination
Comfort Inn & Suites Ambassador Bridge

Comfort Inn & Suites Ambassador Bridge

2.5 out of 5
2330 Huron Church Rd Windsor ON
Fully refundable
The price is €78 per night from 19 Jul to 20 Jul
€78
19 Jul - 20 Jul
includes taxes & fees
8/10 Very good! (1,485 reviews)
"Room is clean, staff very helpful, parking not bad, i can say bfast is typical for most hotels. The only thing i could comment is since the building and rooms a little bit old, a spray of air freshener will help a lot to remove some musty odor."

Reviewed on 2 Jul 2026

Comfort Inn & Suites Ambassador Bridge
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.

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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.