Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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

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 2.594.509 ₫ per night from 29 Jun to 30 Jun
2.594.509 ₫
3.107.704 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (1,014 reviews)
"Love the view"

Reviewed on 22 Jun 2025

Best Western Plus Waterfront Hotel
Caesars Windsor
Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
The price is 3.226.920 ₫ per night from 29 Jun to 30 Jun
3.226.920 ₫
4.342.136 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very Good! (2,988 reviews)
"Stay and accommodations were nice. I’d only say that the while the bathroom was clean it was a bit dated style wise and had no fan. I’d stay again though."

Reviewed on 23 Jun 2025

Caesars Windsor
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 2.568.391 ₫ per night from 13 Jul to 14 Jul
2.568.391 ₫
3.076.419 ₫ total
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very Good! (1,234 reviews)
"Perfect downtown location. Close to casino!"

Reviewed on 20 Jun 2025

Holiday Inn Express Windsor Waterfront by IHG
See all 361 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.

Frequently asked questions

How much does a Windsor holiday package cost?
You'll find cheap prices on Expedia for your Windsor getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor holiday package, consider visiting in January, February and April. You'll generally find lower rates on hotels and airfares during these quieter months --- ideal for a budget-friendly break.
How many days is enough for Windsor?
To fully enjoy your Windsor holiday, we suggest staying for 2 days. Split your time between discovering Chrysler Theatre, Walkerville Brewery and other well-known attractions, as well as experiencing neighbourhoods like East Windsor and Walkerville. If you've got some time to spare, include a day trip in your Windsor holiday itinerary.
Is it worth booking a holiday package to Windsor?
Windsor offers everything you need for an unforgettable getaway. Get your Windsor holiday off to a flying start by checking out top attractions like Adventure Bay Family Water Park.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you're considering a spontaneous Windsor getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Windsor?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Windsor.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your accommodation will probably be the largest expense during your trip to Windsor.
  3. Decide how long to go for: Now that you know more about Windsor, you can work out the perfect length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Windsor holiday package that brings all your bookings together.

Popular places to visit

Caesars Windsor

Caesars Windsor

4.5/5(2 reviews)

Why not try your luck with a visit to Caesars Windsor during your time in Windsor? Stroll along the riverfront or visit the casinos in this vibrant area.

Caesars Windsor
Windsor Riverfront

Windsor Riverfront

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

Windsor Riverfront

Detroit Windsor Tunnel

5/5(1 review)

Find out about the history of Windsor with a stop at Detroit Windsor Tunnel. Stroll along the riverfront or experience the great live music in this vibrant area.

Detroit Windsor Tunnel