Downtown Windsor Vacation Packages
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Top Holiday Package Deals in Downtown Windsor
Price found within the past 48 hours. Click for updated prices.
Hotel STRY
per person
Sep 8 - Sep 12
just found
Roundtrip non-stop flight included
Ottawa (YOW) to Windsor (YQG)
10/10 Exceptional! (11 reviews)
5 Star Rating! The service at The Stry Hotel was outstanding! Amy and her team helped take the best care of our family, everything was beautiful. Highly Recommend!!!
Reviewed on Jul. 3, 2025
Where to stay in Downtown Windsor
Find the best Downtown Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Windsor
City Centre
2 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.
Downtown Windsor Hotel Deals
Best Western Plus Waterfront Hotel
277 Riverside Drive West, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Aug 25 to Aug 26
CA $155
CA $186 total
Aug 25 - Aug 26
includes taxes & fees
8/10 Very Good! (1,015 reviews)
"Clean, friendly staff, location"
Reviewed on Aug. 3, 2025
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East, Windsor, ON
Fully refundable
The price is CA $123 per night from Aug 10 to Aug 11
CA $123
CA $147 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (1,272 reviews)
"Decent hotel...rooms are close...views are not nice unless river view."
Reviewed on Jul. 30, 2025
DoubleTree by Hilton Windsor Hotel & Suites
333 Riverside Dr W, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Aug 17 to Aug 18
CA $165
CA $198 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"The Riverview was absolutely stunning!! I highly recommend"
Reviewed on Aug. 1, 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 Downtown Windsor
Dieppe Gardens
Enjoy a stop at Dieppe Gardens, an entertaining place to visit in Windsor. Stroll along the riverfront or visit the casinos in this vibrant area.
Detroit Windsor Tunnel
Find out about the history of Windsor when you spend time at Detroit Windsor Tunnel. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Adventure Bay Family Water Park
Bring the kiddos to Adventure Bay Family Water Park and enjoy some excitement at this amusement park in Windsor.
Things to do
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
CA $36
per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
CA $185
per adult
Best Downtown Detroit Historical Walking Tour
CA $144
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.