Windsor Holidays

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Your Windsor Holiday

When you book a holiday package to Windsor, all the organising is taken care of beforehand. This gives you more time to discover some of the best things about this riverfront city, such as its cosmopolitan vibe, diversity and friendly locals. You'll want to sightsee during your trip to Windsor. Carve out some time for big-name attractions such as Detroit Windsor Tunnel, Caesars Casino and Caesars Windsor. Expedia is here to help you escape your routine. Tailor your holiday to Windsor to suit your travel style, whatever that may look like.

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 offers a delightful blend of activities perfect for romantic getaways, family holidays, or city explorations. Enjoy educational experiences, captivating theatre productions, and a thrilling water park. Don't miss the chance to explore the fantastic Legoland Windsor for an unforgettable staycation that delights visitors of all ages.

Shopping

Windsor offers a delightful shopping experience with Devonshire Mall, a bustling centre filled with entertainment and family vibes. If you're up for a drive, the nearby Lakeside Shopping Centre features a variety of shops and dining options, perfect for unique gifts and souvenirs.

Recreation

Experience a round at the Ambassador Golf Club, where you can enjoy the lush greens and outdoor atmosphere. For a cultural evening, catch a performance at Chrysler Theatre, offering a blend of romance and entertainment. Alternatively, unwind with a film at Landmark Cinemas Windsor, perfect for family outings.

Adventure

At Adventure Bay Family Water Park in Windsor, enjoy thrilling water slides and wave pools, perfect for family fun. Explore the scenic Mic Mac Park Walking Trails for a refreshing hike through nature. Alternatively, discover the beautiful East Riverside Park Trails, offering picturesque views and outdoor adventure.

Nightlife

Windsor's nightlife offers vibrant experiences along Ouellette Avenue, featuring lively bars and clubs like The Loop and The Windsor Beer Exchange. Enjoy live music, dance the night away, or relax in a pub atmosphere. The waterfront also hosts charming spots for evening strolls and gatherings.

*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 mix of romantic escapes, urban experiences, and family-friendly activities. Visitors can explore captivating attractions like Windsor Castle, Windsor Great Park, Royal Windsor, and Windsor Racecourse. With its vibrant streets, urban parks, and entertainment venues, Windsor is perfect for those seeking outdoor adventures or city-themed outings. Enjoy the charm of this lovely city, ensuring a memorable holiday experience for every traveller.

  • Detroit Windsor Tunnel: Experience the unique thrill of crossing the Detroit Windsor Tunnel, an underground route connecting Canada and the USA. This bustling street captures the vibrant city atmosphere, with its lively surroundings showcasing the local culture and energy.
  • Ambassador Bridge: As an iconic symbol of cross-border connection, the Ambassador Bridge offers rich cultural significance. Stroll along this historic bridge, where you can appreciate its architectural beauty and the stunning views of the Detroit River, embodying the spirit of friendship between nations.
  • University of Windsor: Visit this esteemed institution, known for its lush campus and historical significance. The University of Windsor is not only a hub for education but also a centre for cultural events, making it a vibrant spot for art and community engagement.

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 SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnySlightly HighAverage
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 SunnyAverageSlightly 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 CloudySlightly LowAverage

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 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, Walkerville Brewery and Chrysler Theatre

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 £107 per night from 6 Apr to 7 Apr
£107
6 Apr - 7 Apr
includes taxes & fees
8.6/10 Excellent! (3,176 reviews)
Casino floor was clean and well staffed, especially for table games. Don't confuse Caesars Windsor with Las Vegas, they are not the same. I was hoping for more amenities - no bathrobe or slippers and no in room food service.

Reviewed on 30 Mar 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
The price is £85 per night from 19 Apr to 20 Apr
£85
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (1,358 reviews)
The hotel claims the rooms are soundproof. They are not.

Reviewed on 30 Mar 2026

Holiday Inn Express Windsor Waterfront by IHG
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 £77 per night from 2 Apr to 3 Apr
£77
2 Apr - 3 Apr
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Terrible signage, hard to locate front door. Parking is terrible. Elevators are slow and can take upwards of 10+ minutes to get a working elevator.

Reviewed on 30 Mar 2026

Best Western Plus Waterfront Hotel
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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What to do in Windsor

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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. Flight-inclusive packages are ATOL protected.