Windsor Vacations from ￥270,938

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The Latest Windsor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Caesars Windsor

Caesars Windsor

4 out of 5
City Centre
per person
Aug 8 - Aug 13
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Windsor (YQG)
8.6/10 Excellent! (2,993 reviews)
Great quick trip across the border. We had a great time! Everyone was very friendly and the area is beautiful! The room had a great view and was so clean and spacious!

Reviewed on Jul 4, 2025

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

3 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

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 ￥12,100 per night from Aug 3 to Aug 4
￥12,100
￥14,493 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"You should have advised that the staff was on strike!"

Reviewed on Jul 3, 2025

Best Western Plus Waterfront Hotel
Caesars Windsor
Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
The price is ￥16,161 per night from Jul 13 to Jul 14
￥16,161
￥22,013 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (2,997 reviews)
Great hotel but the Casino not so great
"The hotel was great! The room was roomy, clean and great AC! The bed was very comfortable. The casino on the other hand was just okay. Lots of people playing but very few were winning at all. Not even lots of people getting bonuses on the slots. Great hotel to stay at but avoid the casino at all ..."

Reviewed on Jul 3, 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 ￥17,516 per night from Jul 13 to Jul 14
￥17,516
￥20,981 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The attention to detail and genuine care from the team truly set this hotel apart."

Reviewed on Jul 3, 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.

Discover the most popular places to visit in 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 entertainment choices in this vibrant area.

Ambassador Bridge

Detroit Windsor Tunnel

4/5(364 reviews)

Find out about the history of Windsor when you spend time at Detroit Windsor Tunnel. Stroll along the riverfront or experience the great live music in this vibrant area.

Detroit Windsor Tunnel

University of Windsor

4/5(32 reviews)

Enjoy the collegiate vibe at University of Windsor during your stay in Windsor. Amble around this vibrant area's riverfront or experience its acclaimed art scene.

University of Windsor

What to do in Windsor

Explore undiscovered beauty of Detroit

Explore undiscovered beauty of Detroit

￥19,528
per adult
Explore undiscovered beauty of Detroit
Downtown Detroit Donut and Pastry Adventure

Downtown Detroit Donut and Pastry Adventure

￥10,121
per adult
Downtown Detroit Donut and Pastry Adventure
Explore Michigan Private Half-Day Walking Tour

Best Downtown Detroit Historical Walking Tour

￥15,188
per adult
Best Downtown Detroit Historical Walking Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from ￥270,938 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.