Windsor Vacations

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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

Downtown Windsor

4 out of top 10 points of interest in this area

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

Find hotels in Downtown Windsor

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is ₩145,432 per night from Sep 1 to Sep 2
₩145,432
₩199,352 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (3,043 reviews)
"Yes, I am strongly recommend Caesars hotel. I give 5 stars."

Reviewed on Aug 2, 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 ₩164,202 per night from Aug 10 to Aug 11
₩164,202
₩196,681 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"My husband and I stayed here in July 2025 for a weekend. It was close to the casino and there is also an indoor Waterpark within walking distance. It’s also walking distance to a lot of great restaurants. The room was clean and comfortable."

Reviewed on Aug 5, 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 ₩123,756 per night from Aug 10 to Aug 11
₩123,756
₩148,234 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (1,280 reviews)
I liked it, would go back
"Nice hotel, room was a little small. Nice view of river. Would go back."

Reviewed on Aug 5, 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 374 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.

Discover the most popular places to visit in Windsor

Olde Walkerville Neighborhood

Enjoy a stop at Olde Walkerville Neighborhood, an entertaining place to visit in Windsor. Discover the great live music and casinos in this vibrant area.

Olde Walkerville Neighborhood

Walkerville Brewery

4/5(1 review)

You can take time to visit Walkerville Brewery during your travels to Windsor.

Walkerville Brewery

Frequently asked questions

How much does a Windsor vacation 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 vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation 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 vacation, we suggest staying for 2 days. Split your time between discovering Chrysler Theatre, Walkerville Brewery and other well-known attractions, as well as experiencing neighborhoods like East Windsor and Walkerville. If you've got some time to spare, include a day trip in your Windsor vacation itinerary.
Is it worth booking a vacation package to Windsor?
Windsor offers everything you need for an unforgettable getaway. Get your Windsor vacation 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 personalize 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 vacation as a package?
Expedia vacation 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 customized Windsor vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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 accommodations 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 vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.