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
Windsor featuring signage

City Centre

6 out of top 10 points of interest in this area

If you're spending some time in City Centre, Detroit Windsor Tunnel and Chrysler Theatre are top sights worth seeing.

Find hotels in City Centre

Top hotels in Windsor

Caesars Windsor
Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
The price is €135 per night from 3 Apr to 4 Apr
€135
includes taxes & fees
3 Apr - 4 Apr
8.4/10 Very Good! (2,777 reviews)
"Friendly staff and clean"

Reviewed on 24 Mar 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
Fully refundableReserve now, pay when you stay
The price is €128 per night from 20 Apr to 21 Apr
€128
includes taxes & fees
20 Apr - 21 Apr
8.8/10 Excellent! (1,000 reviews)
"Amazing"

Reviewed on 24 Mar 2025

DoubleTree by Hilton Windsor Hotel & Suites
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 €108 per night from 20 Apr to 21 Apr
€108
includes taxes & fees
20 Apr - 21 Apr
8.4/10 Very Good! (1,178 reviews)
"The staff offered my 2 sons a bag full of chocolates and water."

Reviewed on 23 Mar 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 347 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.

Frequently asked questions

How much does a Windsor holiday package cost?
You’ll find cheap prices on Expedia for your Windsor getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
If you’re looking to snag a cheap Windsor holiday package, consider visiting in January, February and April. You’ll generally find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Windsor?
To fully enjoy your Windsor holiday, we suggest staying for 2 days. Split your time between discovering Chrysler Theatre, Walkerville Brewery and other well-known attractions, as well as experiencing neighbourhoods like East Windsor and Walkerville. If you’ve got some time to spare, include a day trip in your Windsor holiday itinerary.
Is it worth booking a holiday package to Windsor?
Windsor offers everything you need for an unforgettable getaway. Get your Windsor holiday off to a flying start by checking out top attractions like Adventure Bay Family Water Park.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is easy with Expedia. Once you’ve entered your destination and travel dates under our “Packages” tab, set your budget, apply a couple of filters and browse what’s available. You can personalise your search by “Popular locations,” “Property type,” “Guest rating” and more. Sort the results by “Price: low to high” to discover the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You’ll typically snag a better deal than booking each component individually. And you’ll still have the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you’re considering a spontaneous Windsor getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Windsor?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Windsor.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your accommodation will probably be the largest expense during your trip to Windsor.
  3. Decide how long to go for: Now that you know more about Windsor, you can work out the perfect length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that’s left is to find a Windsor holiday package that brings all your bookings together.

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

€29
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Fall walleye from the Detroit River @ Wyandotte MI.

Fishing Detroit

€300
per adult
Fishing Detroit
Detroit: Architectural Beauty and Hidden Gems Walking Tour

Detroit: Architectural Beauty and Hidden Gems Walking Tour

€125
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.