Downtown Windsor Vacations from $323
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The Latest Downtown Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Windsor Ambassador Bridge by IHG
Sandwich
Price was $381, price is now $323 per person
$323
per person
Dec 19 - Dec 22
found 11 hours ago
Roundtrip flight included
Houston (HOU) to Windsor (YQG)
7.6/10 Good! (1,006 reviews)
Great 2 nights, clean hotel. Quiet and front desk staff were attentive and welcoming, when I checked in it was seamless and when I checked out they were prepared with my paper work. I will be staying again.
Reviewed on Nov 6, 2025
Hotel STRY
Price was $591, price is now $476 per person
$476
per person
Dec 19 - Dec 22
found 11 hours ago
Roundtrip flight included
Houston (HOU) to Windsor (YQG)
9.8/10 Exceptional! (20 reviews)
Absoultely enjoyed our stay. Sucess is always based on attention to details, in any business, and every detail here is well thought out. Look forward to many more visits.
Reviewed on Oct 10, 2025
Caesars Windsor - A Caesars Rewards Destination
City Centre
Price was $534, price is now $435 per person
$435
per person
Dec 19 - Dec 22
found 11 hours ago
Roundtrip flight included
Houston (HOU) to Windsor (YQG)
8.6/10 Excellent! (3,091 reviews)
Clean rooms and beautiful view from room.
Reviewed on Nov 16, 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
$65 nightly
The price is $78 total per night from Nov 23 to Nov 24
$78 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
Courteous staff, comfortable room
Reviewed on Nov 13, 2025
DoubleTree by Hilton Windsor Hotel & Suites
333 Riverside Dr W, Windsor, ON
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $139 total per night from Dec 3 to Dec 4
$139 total
Dec 3 - Dec 4
Total with taxes and fees
9/10 Wonderful! (1,036 reviews)
Comfortable as always
Reviewed on Nov 11, 2025
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East, Windsor, ON
Fully refundable
$103 nightly
The price is $123 total per night from Nov 20 to Nov 21
$123 total
Nov 20 - Nov 21
Total with taxes and fees
8.6/10 Excellent! (1,355 reviews)
Everything was good clean and organized.
Reviewed on Nov 13, 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
Macabre, Murder, & Mayhem in Motor City : Detroit Ghost Tour
$26
per adult
Downtown Detroit Delicious Donut, Coffee, & Pastry Adventure
$70
per adult
Best Downtown Detroit Historical Walking Tour
$105
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.