Downtown Windsor Vacations from $402
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The Latest Downtown Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Dream BNB Estate Inn and Retreat House
Price was $543, price is now $494 per person
$494
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Windsor (YQG)
9.6/10 Exceptional! (106 reviews)
This property was clean and comfortable. It had everything I needed for my short stay. The construction outside was a little tricky but I was warned about the detour.
Reviewed on Sep 29, 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
Walkerville
Heritage precinct with large houses, wide streets, and abundant greenery, Walkerville boasts attractions like Willistead Manor, the Via Rail station, and the recently reopened Old Walkerville Theatre.
Downtown Windsor Hotel Deals
Best Western Plus Waterfront Hotel
277 Riverside Drive West, Windsor, ON
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $116 total per night from Oct 5 to Oct 6
$116 total
Oct 5 - Oct 6
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Everything"
Reviewed on Sep 25, 2025
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East, Windsor, ON
Fully refundable
$116 nightly
The price is $139 total per night from Oct 12 to Oct 13
$139 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,340 reviews)
"The room was a bit small and they had the tv infront of one bed only and a dresser right beside it so you couldn’t really see the tv from the other bed. Staff were great, beds comfy, pillows nice, view of city was good, the area was cute right by the water and a walking area to go sit and look at ..."
Reviewed on Sep 28, 2025
DoubleTree by Hilton Windsor Hotel & Suites
333 Riverside Dr W, Windsor, ON
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $142 total per night from Oct 12 to Oct 13
$142 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
"Upon check the very friendly staff gave us two large warm chocolate cookies .such a nice tough. The room was modern and clean"
Reviewed on Sep 22, 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
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 acclaimed art scene in this vibrant area.
Adventure Bay Family Water Park
4/5(1 review)
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
$32
per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
$135
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.