
Windsor Vacations from ¥270,938
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Caesars Windsor
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

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 the Best Windsor Vacation Packages
Windsor Hotel Deals

Best Western Plus Waterfront Hotel
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

Caesars Windsor
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

DoubleTree by Hilton Windsor Hotel & Suites
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
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
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.
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.
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.
What to do in Windsor

Downtown Detroit Donut and Pastry Adventure
¥10,121
per adult

Best Downtown Detroit Historical Walking Tour
¥15,188
per adult
Frequently asked questions
Other vacations you might like
Expedia's Latest Trends
Packages
General
Visit VictoriaVisit YellowknifeVisit ChilliwackVisit Niagara-on-the-LakeVisit CastlegarVisit Red DeerVisit MonctonVisit AbbotsfordVisit Lake LouiseVisit UclueletVisit PentictonVisit IqaluitVisit NanaimoVisit NelsonVisit BanffVisit DrumhellerVisit District of North VancouverVisit LethbridgeVisit Niagara FallsVisit St. John'sVisit HalifaxVisit Mont-TremblantVisit Sherbrooke
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.