Windsor Holidays

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Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Windsor showing signage

Downtown Windsor

4 out of top 10 points of interest in this area

While visiting Downtown Windsor, you might make a stop by sights like Detroit Windsor Tunnel and Chrysler Theatre.

Find hotels in Downtown Windsor

Top hotels in Windsor

Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is S$196 per night from 6 Nov to 7 Nov
S$196
6 Nov - 7 Nov
includes taxes & fees
8.6/10 Excellent! (3,102 reviews)
The Room Was very nice and well kept

Reviewed on 27 Oct, 2025

Caesars Windsor - A Caesars Rewards Destination
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 S$103 per night from 30 Nov to 1 Dec
S$103
30 Nov - 1 Dec
includes taxes & fees
8/10 Very Good! (1,018 reviews)
My river view room was spectacular. The Detroit skyline, Belle Isle to the Ambassador. What a panorama. Good desk for working, comfortable easy chair, nice coffee bar. I could live here.

Reviewed on 28 Oct, 2025

Best Western Plus Waterfront Hotel
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 S$184 per night from 16 Nov to 17 Nov
S$184
16 Nov - 17 Nov
includes taxes & fees
9/10 Wonderful! (1,030 reviews)
The breakfast unfortunately was not included in our stay it also didn’t give us the option not sure if it was due to Expedia or the hotel that was pretty much only downside, other than that stay was nice hotel seemed clean somewhat close to everything in city all in all decent stay.

Reviewed on 23 Oct, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 387 properties in Windsor
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.

What to do in Windsor

Step into the shadows and discover the haunting tales of Motor City's past.

Macabre, Murder, & Mayhem in Motor City : Detroit Ghost Tour

S$33
per adult
Macabre, Murder, & Mayhem in Motor City : Detroit Ghost Tour
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

S$88
per adult
Roasting Experience at 14th Coffee Co
Private Downtown Detroit Helicopter Ride

Private Downtown Detroit Helicopter Ride

S$194
per adult
Private Downtown Detroit Helicopter Ride
See all activities in Windsor

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.