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

3 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

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$104 per night from 4 Jan to 5 Jan
S$104
4 Jan - 5 Jan, 2026
includes taxes & fees
8/10 Very Good! (1,015 reviews)
Clean room & attentive staff

Reviewed on 15 Dec, 2025

Best Western Plus Waterfront Hotel
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$197 per night from 16 Dec to 17 Dec
S$197
16 Dec - 17 Dec
includes taxes & fees
8.6/10 Excellent! (3,160 reviews)
Room was nice and clean

Reviewed on 15 Dec, 2025

Caesars Windsor - A Caesars Rewards Destination
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$179 per night from 28 Dec to 29 Dec
S$179
28 Dec - 29 Dec
includes taxes & fees
9/10 Wonderful! (1,044 reviews)
Clean room…friendly staff…prompt response from housekeeping

Reviewed on 12 Dec, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 388 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

Detroit Red Wings Ice Hockey Game at Little Caesars Arena

Detroit Red Wings Ice Hockey Game at Little Caesars Arena

S$71
per adult
Detroit Red Wings Ice Hockey Game at Little Caesars Arena
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

S$89
per adult
Roasting Experience at 14th Coffee Co
Step into the shadows and discover the haunting tales of Motor City's past.

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

S$41
per adult
Macabre, Murder, & Mayhem in Motor City : Detroit Ghost Tour
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.