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$196 per night from 23 Feb to 24 Feb
S$196
23 Feb - 24 Feb
includes taxes & fees
8.6/10 Excellent! (3,209 reviews)
Amazing staff, live music and total vibe in Arius club. My hisband enjoyed his birthday in Canada 🇨🇦

Reviewed on 25 Jan, 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 S$104 per night from 8 Feb to 9 Feb
S$104
8 Feb - 9 Feb
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Amazing stay! Stayed with toddlers and we all had a great time!

Reviewed on 29 Jan, 2026

Best Western Plus Waterfront Hotel
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$178 per night from 22 Feb to 23 Feb
S$178
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (1,071 reviews)
room was clean staff friendly

Reviewed on 29 Jan, 2026

DoubleTree by Hilton Windsor Hotel & Suites
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.