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
Windsor featuring signage

Downtown Windsor

4 out of top 10 points of interest in this area

While visiting Downtown Windsor, you might make a stop by sights like Detroit Windsor Tunnel and Chrysler Theatre.

Find hotels in Downtown Windsor

Things to do in Windsor

Windsor offers a delightful blend of activities perfect for romantic getaways and family vacations. Enjoy a visit to the renowned Legoland Windsor, which promises an exciting staycation filled with educational fun. You can also explore the local theatre scene and unwind at the water park. With its vibrant city atmosphere, Windsor is sure to provide a memorable experience for every tourist.

Shopping

If you're up for a drive, head to Devonshire Mall, a vibrant shopping centre in Windsor offering a mix of entertainment and family-friendly vibes. You'll find a variety of shops perfect for gifts and souvenirs, making it a delightful stop during your visit.

Recreation

At the Ambassador Golf Club, enjoy a day on the greens surrounded by natural beauty, perfect for relaxation and fresh air. Chrysler Theatre offers cultural experiences with romantic performances, while Landmark Cinemas Windsor provides family-friendly entertainment, making it ideal for a leisurely evening out.

Adventure

At Adventure Bay Family Water Park in Windsor, enjoy exhilarating water slides and splash zones, perfect for families seeking fun and excitement. Explore the scenic Mic Mac Park Walking Trails for a refreshing hike surrounded by nature, or venture along the East Riverside Park Trails to soak in stunning riverside views.

Nightlife

Windsor's nightlife is vibrant, featuring an array of bars and clubs. Visit The Cook's Shop for a lively atmosphere and exquisite cocktails. For dancing, head to The Lounge at Caesars Windsor, where you can enjoy live entertainment and a lively crowd.

*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 and family-friendly attractions, making it ideal for city-themed vacations. Visitors can explore urban parks, entertainment arenas, and notable sites such as Windsor Great Park, Windsor Castle, Royal Windsor, and Windsor Racecourse. Whether you seek outdoor experiences or engaging city adventures, Windsor has something for everyone.

  • The Colosseum: Experience the vibrant atmosphere of this premier entertainment venue in Windsor, hosting everything from concerts to sports events. It's a perfect spot for families seeking thrilling entertainment and unforgettable memories.
  • Art Gallery of Windsor: Immerse yourself in the rich cultural scene at this esteemed arts centre, showcasing a diverse collection of Canadian and international art. The gallery offers a tranquil space for art enthusiasts and casual visitors alike to appreciate creativity.
  • Detroit Windsor Tunnel: Travel through this iconic underground route connecting Windsor and Detroit. The tunnel provides a unique urban experience, allowing you to marvel at the engineering while enjoying views of the bustling city life on both sides.

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 with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.3°F (-3.7°C)Light RainMostlySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostlySlightly LowSlightly Low
March36.3°F (2.4°C)Light RainMostlyAverageSlightly 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 RainMostlySlightly LowAverage

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 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

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is £111 per night from 1 Sept to 2 Sept
£111
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (3,015 reviews)
"Nice spacious room with a great view. There’s some great dining options on the property. Spagos was great. Celebrated my 50th birthday."

Reviewed on 14 Aug 2025

Caesars 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 £104 per night from 18 Aug to 19 Aug
£104
18 Aug - 19 Aug
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"There was some mold in the closet , itried to get an extra pillow but decided against it when i saw the mold, and the barth tub had some kind of dark stains , not quit sure what it was ? apart from that my stay was ok, I will stay again in a diffrent room.thank you"

Reviewed on 15 Aug 2025

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 £91 per night from 21 Aug to 22 Aug
£91
21 Aug - 22 Aug
includes taxes & fees
8.6/10 Excellent! (1,295 reviews)
"Staff and location"

Reviewed on 14 Aug 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 388 properties in Windsor
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Caesars Casino

Caesars Casino

5/5(1 review)

Why not try your luck with a visit to Caesars Casino during your travels in Windsor? Discover the top-notch restaurants and acclaimed theatre scene in this family-friendly area.

Caesars Casino

Adventure Bay Family Water Park

Bring the children to Adventure Bay Family Water Park and enjoy this exciting theme park in Windsor.

Adventure Bay Family Water Park

What to do in Windsor

Step into the shadows and discover the haunting tales of Motor City's past.

Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

£19
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Detroit: Architectural Beauty and Hidden Gems Walking Tour

Detroit: Architectural Beauty and Hidden Gems Walking Tour

£100
per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
Explore Michigan Private Half-Day Walking Tour

Best Downtown Detroit Historical Walking Tour

£78
per adult
Best Downtown Detroit Historical Walking Tour
See all activities in Windsor

Frequently asked questions

Why should I book my Windsor holiday with Expedia?
Choose Expedia to plan your next big adventure simply and all in one place. Our top tip for bagging a great deal on a Windsor retreat? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a few fun tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to worry if you have to switch up your travel plans. Round-the-clock help with cancelling and changing your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Windsor?
If you enjoy the excitement that comes with peak season, head to Windsor in May, July and August. If you're looking for a calmer vibe, December, January and February will suit you better. To give you an idea of the type of weather you can experience, the daytime average temperature in January, the coolest time of year in Windsor, is -3ºC. The warmest period here is July, when temperatures average 23ºC.
What are the top hotels for my holiday in Windsor?
If you're thinking of staying in the Walkerville neighbourhood, Best Western Plus Waterfront Hotel and Super 8 by Wyndham Windsor/Dougall are in-demand options. East Windsor is also a favourite Windsor area. We recommend Hampton Inn & Suites by Hilton Windsor or Caesars Windsor if you choose this end of town.
How do I get a cheap holiday to Windsor?
Combine your flights and hotels, throw in extras such as tours, and save with a Windsor holiday. You won't just score wonderful discounts on your escape — you'll have plenty of choice at your fingertips too. When you book with Expedia, you'll have your pick of over 400 air carriers and 321,000 properties globally. Your next epic adventure starts right here, right now! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Windsor holiday?
Make sure your next holiday in Windsor is one to remember by checking out its top attractions. Detroit Windsor Tunnel, Caesars Casino, Caesars Windsor and University of Windsor are just some of the things you should see while you're here.
What is the best area to stay in when on holiday in Windsor?
If you plan to check out Detroit Windsor Tunnel, save yourself the hassle of commuting and find somewhere to stay close by. It's one of the best attractions in Windsor.
Do I need a visa for my Windsor holiday?
Official government websites have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and reason for your visit, whether it be for holidays or work, will determine if you'll need a visa for Windsor. Also double-check that your passport is up to date and has a minimum of six months validity remaining after the date of your return. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Windsor holiday?
Think about the types of activities you'll be doing during your Windsor trip and travel with pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse style blogs or social media accounts. Take a look at the weather forecast so you can pack appropriately. The warmest time of year in Windsor is July, with average daytime temperatures of 23ºC. If you're visiting during the coolest month of January, the mercury averages -3ºC during the day.
What does an Expedia Windsor holiday include?
Flights, hotels and car hires, or any combination of the three — the choice is all yours! Whether you're headed to Windsor on a family road trip or travelling with your friends, there's a bundle to fit every style and budget. Once you've made your booking, why not add on one or two tours or activities? Private holiday homes and apartments are a few of the most popular property types in Windsor. Whatever your holiday style or group size, you can rely on Expedia for the freedom and flexibility to customise your next dream escape.
Does Expedia offer Book Now, Pay Later Windsor holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that suits you best during checkout and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying in multiple instalments works for you, pick this option at checkout.
  • No-deposit holidays: Pressing the "book now" button is easier with this payment plan. With no upfront fee for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Windsor Expedia holiday?
Yes, the choice is all yours. Expedia has access to more than 400 airlines across the globe, so you can tailor your Windsor holiday according to your needs and budget.

* 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.