Downtown Windsor Vacations from $1,020
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The Latest Downtown Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Dream Estate Inn
Price was $1,108, price is now $1,020 per person
$1,020
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
9.4/10 Exceptional! (142 reviews)
Turn in to property driveway is awkward when approaching from WB Seacliffe and borderline unsafe when coming EB from the roundabout.
Remember- Leamington drivers can often be unpredictable.
Reviewed on Oct 19, 2026
Hotel STRY
Price was $1,180, price is now $1,049 per person
$1,049
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
10/10 Exceptional! (46 reviews)
I almost don’t want to share how spectacular Hotel STRY is! I will make a point to book this hotel every single time I am in this area. I will drive from Windsor just to stay here. If you have the pleasure of meeting Cat, she is amazing and will take care of all your needs. This is a Must Stay if you are anywhere near Amherstburg!
Reviewed on Oct 30, 2026
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
$95 nightly
The price is $114 total per night from Nov 18 to Nov 19
$114 total
Nov 18 - Nov 19
Total with taxes and fees
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East Windsor ON
Fully refundable
$96 nightly
The price is $114 total per night from Dec 8 to Dec 9
$114 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (1,492 reviews)
"Everything perfectly fine"
Reviewed on Nov 9, 2026
DoubleTree by Hilton Windsor Hotel & Suites
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $129 total per night from Nov 29 to Nov 30
$129 total
Nov 29 - Nov 30
Total with taxes and fees
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.
Stay near popular Downtown Windsor attractions
Things to do
Macabre, Murder, & Mayhem in Motor City : Detroit Ghost Tour
$26
per adult
Self Guided Detroit's Spirit and History Solo Walking Tour
$10
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.