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.

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

Our guide on where to stay in Windsor

Check out a few of the areas and neighbourhoods we love in Windsor Learn more about Windsor
Windsor featuring signage

Downtown Windsor

3 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

Our pick of the best Windsor Hotel Deals

Best Western Plus Waterfront Hotel
Best Western Plus Waterfront Hotel
2.5 out of 5
277 Riverside Drive West, Windsor, ON
Stay at this business-friendly hotel in Windsor. Enjoy breakfast (surcharge), a fitness centre and parking (surcharge). Our guests praise the helpful staff in ...
8/10 Very Good! (1,003 reviews)
"Great experience over all. Rooms are not really up to date (at least ours wasn’t). Burn marks on the carpet and just room wine was not modern. Great location tho."

Reviewed on 24 Jun 2025

Best Western Plus Waterfront Hotel
Caesars Windsor
Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
Stay at this 4-star business-friendly hotel in Windsor. Enjoy free Wi-Fi, free parking and 6 restaurants. Our guests praise the bar and the helpful staff in ...
8.4/10 Very Good! (2,997 reviews)
"Good"

Reviewed on 27 Jun 2025

Caesars Windsor
DoubleTree by Hilton Windsor Hotel & Suites
DoubleTree by Hilton Windsor Hotel & Suites
4 out of 5
333 Riverside Dr W, Windsor, ON
Stay at this business-friendly hotel in Windsor. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,004 reviews)
"Had an amazing experience at the Hilton Doubletree in Windsor Ont. The room had the most stunning view of metro Detroit and the Bridge. The River Room Restraunt was top notch."

Reviewed on 24 Jun 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 367 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

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.

Discover the most popular places to visit in Windsor

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 vibrant 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

Unmissable things 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

£24
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Explore Michigan Private Half-Day Walking Tour

Best Downtown Detroit Historical Walking Tour

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

* 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.