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
A city skyline at dusk with illuminated buildings reflecting on the water.

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 Caesars Casino and Detroit Windsor Tunnel.

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 Rp1.585.858 per night from 29 Jul to 30 Jul
Rp1.585.858
Rp1.899.541 total
29 Jul - 30 Jul
includes taxes & fees
8.2/10 Very good! (1,105 reviews)
"Very beautiful view! Def. Would book again"

Reviewed on 15 Jul 2026

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 Rp1.016.506 per night from 20 Jul to 21 Jul
Rp1.016.506
Rp1.539.245 total
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (3,280 reviews)
"All was excellent. However we did have some difficulty finding our way around the complex."

Reviewed on 15 Jul 2026

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 Rp1.888.618 per night from 10 Aug to 11 Aug
Rp1.888.618
Rp2.262.186 total
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,132 reviews)
"Good location and clean facility."

Reviewed on 15 Jul 2026

DoubleTree by Hilton Windsor Hotel & Suites
See all 438 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.

Stay near popular Windsor attractions

A nighttime view of a hotel with a moon in the sky, a waterfall, and illuminated steps leading to the building.
Photo by Daniel J Bellyk
Open Photo by Daniel J Bellyk

Caesars Casino

8.4/10 (1,170 reviews)
This glittering riverside casino features 100,000 square feet of gaming space with over 2,500 slot machines. Reserve tickets to The Colosseum where international performers take the 5,000-seat stage.
See properties

What to do in Windsor

Detroit Tigers Baseball Game at Comerica Park

Detroit Tigers Baseball Game at Comerica Park

Rp530.967
per adult
Detroit Tigers Baseball Game at Comerica Park
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

Rp1.193.783
per adult
Roasting Experience at 14th Coffee Co
Detroit Downtown Food Tour with 6+ Iconic Tastings in Motor City

Detroit Downtown Food Tour with 6+ Iconic Tastings in Motor City

Rp1.750.182
per adult
Detroit Downtown Food Tour with 6+ Iconic Tastings in Motor City
See all activities in Windsor

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.

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