Downtown Windsor Packages (Flight + Hotel)

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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

Top hotels in Downtown Windsor

DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
The price is ฿3,382 per night from 26 May to 27 May
฿3,382
฿4,051 total
26 May - 27 May
includes taxes & fees
9.2/10 Wonderful! (1,091 reviews)
Check in was easy. We were given directions to the parking area, right behind the building, and the ticket to use for going in and out. The third level of the parking garage has the enclosed walkway that takes you directly back to the hotel. We were pleasantly surprised by the wonderful view when ...

Reviewed on 8 May 2026

DoubleTree by Hilton Windsor Hotel & Suites
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
The price is ฿3,162 per night from 3 Jun to 4 Jun
฿3,162
฿3,788 total
3 Jun - 4 Jun
includes taxes & fees
8.2/10 Very Good! (1,015 reviews)
We stay here at least once a month. The views are incredible, the rooms are clean and comfortable and the staff is always so welcoming.

Reviewed on 7 May 2026

Best Western Plus Waterfront Hotel
Holiday Inn Express Windsor Waterfront by IHG

Holiday Inn Express Windsor Waterfront by IHG

2.5 out of 5
33 Riverside Drive East Windsor ON
Fully refundable
The price is ฿3,178 per night from 18 May to 19 May
฿3,178
฿3,807 total
18 May - 19 May
includes taxes & fees
8.8/10 Excellent! (1,381 reviews)
It was very good

Reviewed on 8 May 2026

Holiday Inn Express Windsor Waterfront by IHG
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.

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.