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 AED 392 per night from Apr 7 to Apr 8
AED 392
AED 534 total
includes taxes & fees
7 Apr - 8 Apr
8.4/10 Very Good! (2,792 reviews)
"Love staying here!"

Reviewed on 31 March 2025

Caesars Windsor
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 AED 363 per night from Apr 20 to Apr 21
AED 363
AED 434 total
includes taxes & fees
20 Apr - 21 Apr
8.4/10 Very Good! (1,185 reviews)
"Convenient location."

Reviewed on 1 April 2025

Holiday Inn Express Windsor Waterfront by IHG
Comfort Inn & Suites Ambassador Bridge
Comfort Inn & Suites Ambassador Bridge
2.5 out of 5
2330 Huron Church Rd, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is AED 229 per night from Apr 6 to Apr 7
AED 229
AED 283 total
includes taxes & fees
6 Apr - 7 Apr
7.8/10 Good! (1,000 reviews)
"Great location and exceeded expectations with how good the rooms are, and the staff is super friendly!!"

Reviewed on 30 March 2025

Comfort Inn & Suites Ambassador Bridge
See all 352 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 family-friendly 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