Windsor Vacations

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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 featuring signage

Downtown Windsor

3 out of top 10 points of interest in this area

If you're spending some time in Downtown Windsor, Detroit Windsor Tunnel and Chrysler Theatre are top sights worth seeing.

Find hotels in Downtown Windsor

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 AED 249 per night from Jan 4 to Jan 5
AED 249
AED 298 total
4 Jan - 5 January 2026
includes taxes & fees
8/10 Very Good! (1,010 reviews)
.

Reviewed on 26 December 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 AED 409 per night from Jan 4 to Jan 5
AED 409
AED 565 total
4 Jan - 5 January 2026
includes taxes & fees
8.6/10 Excellent! (3,174 reviews)
Clean room

Reviewed on 21 December 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 AED 430 per night from Jan 25 to Jan 26
AED 430
AED 516 total
25 Jan - 26 January 2026
includes taxes & fees
9/10 Wonderful! (1,045 reviews)
Very good

Reviewed on 21 December 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 390 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.

Discover the most popular places to visit in Windsor

Detroit is making a come back and you should see all it has to offer. Take a day to walk down town and the river front. You may be pleasantly surprise by what you see and feel about the motor city. From River days, to the American Auto show, to all the many events at Cobo hall and DTE center Detroit wants to welcome tourists and explorers. https://midlifemilestones.com/downtown-detroit/

Caesars Casino

Why not try your luck with a visit to Caesars Casino during your time in Windsor? Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Caesars Casino
Ambassador Bridge

Ambassador Bridge

You can learn about the history of Windsor with a visit to Ambassador Bridge. Stroll along the riverfront or experience the great live music in this vibrant area.

Ambassador Bridge
Windsor Riverfront showing a sunset, a river or creek and fishing

Windsor Riverfront

After visiting Windsor Riverfront, make a plan to see the other sights and activities in Windsor.

Windsor Riverfront

Frequently asked questions

How do I find cheap flights to Windsor that have flexible change policies?
Search for your low-cost flights to Windsor, then select "No change fee" underneath the "Flexible change policies" filter. It really is that simple. We appreciate that travel plans change and flexibility matters, so you can book with confidence with Expedia.
How can I find cheap tickets to Windsor?
To get your hands on a great deal to Windsor, book well ahead of time. Also consider using Expedia's "flexible dates" link at the top of your search results. This will compare the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Windsor.
How much is a flight to Windsor?
One-way flights taking off from () sold for as low as in the last seven days. During this time, the cost of a return journey to Windsor varied between and . If you spot a bargain, grab it fast — these fares don't stick around.
When is the cheapest time to fly to Windsor?
Taking off on a Tuesday, followed by a Monday, is usually the best way to secure the cheapest fare. Stay away from the weekends if possible, because Saturday is typically the costliest day. Spend the dollars you saved having fun in Windsor instead!
How much is a plane ticket to Windsor?
In the last seven days, plane fares to Windsor fluctuated from to .
What months are the cheapest to book a flight to Windsor?
Grab your ticket in February to enjoy the cheapest flights to Windsor. December is typically the most expensive time to purchase an airfare.