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

City Centre

6 out of top 10 points of interest in this area

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

Find hotels in City Centre

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 SAR 412 per night from May 19 to May 20
SAR 412
SAR 561 total
includes taxes & fees
19 May - 20 May
8.4/10 Very Good! (2,828 reviews)
"Excellent. 10/10"

Reviewed on 27 April 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 SAR 309 per night from May 11 to May 12
SAR 309
SAR 370 total
includes taxes & fees
11 May - 12 May
8/10 Very Good! (1,010 reviews)
"Great view glass needed to be cleaned though"

Reviewed on 27 April 2025

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 SAR 447 per night from May 18 to May 19
SAR 447
SAR 536 total
includes taxes & fees
18 May - 19 May
8.8/10 Excellent! (1,003 reviews)
"Fantastic stay! Our room was clean, spacious, staff was friendly and attentive. The aquatic facility is right across the street. Skywalk connecting parking and hotel. All the pros and no cons. Would definitely stay there again!"

Reviewed on 25 April 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 353 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 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 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.

Discover the most popular places to visit in Windsor

Detroit is making a come back and you should see all it has to offer. Take a day to walk down town and the river front. You may be pleasantly surprise by what you see and feel about the motor city. From River days, to the American Auto show, to all the many events at Cobo hall and DTE center Detroit wants to welcome tourists and explorers. https://midlifemilestones.com/downtown-detroit/

Caesars Casino

4.5/5(68 reviews)

Why not try your luck with a visit to Caesars Casino during your time in Windsor? Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.

Caesars Casino
Caesars Windsor

Caesars Windsor

4.5/5(144 reviews)

Why not try your luck with a visit to Caesars Windsor during your visit to Windsor? Stroll along the riverfront or visit the casinos in this vibrant area.

Caesars Windsor
Ambassador Bridge

Ambassador Bridge

4.5/5(4 reviews)

You can learn about the history of Windsor with a visit to Ambassador Bridge. Stroll along the riverfront or experience the great live music in this vibrant area.

Ambassador Bridge