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 is an ideal destination for romantic getaways, family holidays, and city adventures. Visitors can enjoy a variety of activities, including educational attractions and theatre performances. A standout experience is the Legoland Windsor, perfect for families seeking fun and excitement. Consider an awesome staycation at Legoland Windsor for an unforgettable holiday filled with creativity and adventure.

Shopping

For a delightful shopping experience in Windsor, visit Devonshire Mall, where you’ll find a mix of fashion, entertainment, and family-friendly options. If you're up for a drive, the nearby Tecumseh Mall offers even more retail choices and local shops to explore.

Recreation

Experience captivating performances at Chrysler Theatre, where romance and culture entwine. Enjoy a relaxing day at Ambassador Golf Club, surrounded by picturesque greens and outdoor sports. Alternatively, unwind at Landmark Cinemas Windsor, perfect for family entertainment and romantic movie dates.

Adventure

Adventure Bay Family Water Park offers thrilling water slides and wave pools, perfect for family fun and excitement. For a dose of nature, explore the Odette Sculpture Park Walking Trail and East Riverside Park Trails, both featuring stunning outdoor scenery and adventurous hiking opportunities.

Nightlife

Windsor's nightlife is vibrant, with an array of bars and clubs. Visit The Loop, known for its lively atmosphere and cocktails. For a more relaxed vibe, try The Windsor Beer Exchange, where you can enjoy local brews and live music, making for an unforgettable evening 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, is perfect for romantic getaways, city explorations, and family vacations. Visitors can enjoy a variety of attractions, including the Royal Windsor, Windsor Great Park, Windsor Castle, and Windsor Racecourse, all set within charming streets and urban parks. This city offers a delightful mix of outdoor experiences and urban entertainment, catering to diverse interests and ensuring a memorable visit for all types of travellers.

  • Detroit Windsor Tunnel: Experience the bustling city vibes of the Detroit Windsor Tunnel, a vital connection between Windsor and Detroit. This underground passage offers a unique perspective of urban life as you travel beneath the river, making it a fascinating journey for tourists.
  • Ambassador Bridge: The Ambassador Bridge is a historic landmark that showcases the rich cultural heritage of the area. Spanning the Detroit River, this iconic bridge not only facilitates trade but also offers stunning views and a glimpse into the region's history.
  • University of Windsor: A historic institution, the University of Windsor boasts beautiful architecture and a vibrant campus life. Explore its cultural vibes through various events and exhibitions, making it a great spot for both education and leisure.

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

  • 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 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 S$166 per night from 31 May to 1 Jun
S$166
31 May - 1 Jun
includes taxes & fees
8.6/10 Excellent! (3,206 reviews)
It would of been great if I know how to pick a room on the river. Perhaps your website should tell you the the view is we tried to get a room facing the river but they refuse because we went through your website

Reviewed on 29 Apr, 2026

Caesars Windsor - A Caesars Rewards Destination
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
The price is S$161 per night from 15 May to 16 May
S$161
15 May - 16 May
includes taxes & fees
9.2/10 Wonderful! (1,080 reviews)
Our hotel room was not ready by 4pm. Had to wait in line 3 times to get access to room 30 mins later than what I paid for

Reviewed on 1 May, 2026

DoubleTree by Hilton Windsor Hotel & Suites
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 S$97 per night from 27 May to 28 May
S$97
27 May - 28 May
includes taxes & fees
8/10 Very Good! (1,281 reviews)
Nice hotel. Breakfast was good with hot options. Staff were friendly. Pool liked great although we didn't use it. We would stay again.

Reviewed on 1 May, 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.

What to do in Windsor

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