Windsor Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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$153 per night from 27 Jul to 28 Jul
S$153
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (1,015 reviews)
"The only issue we had is currently the staff is on strike, therefore they where playing loud music at 5am unfortunately the hotel cannot control it, but should give a discounted rate."

Reviewed on 19 Jul, 2025

Best Western Plus Waterfront Hotel
Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is S$204 per night from 21 Jul to 22 Jul
S$204
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very Good! (3,018 reviews)
"The vueon the riverside drive very beautihul"

Reviewed on 17 Jul, 2025

Caesars Windsor
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$185 per night from 3 Aug to 4 Aug
S$185
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"great place to stay"

Reviewed on 14 Jul, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 366 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

Private Downtown Detroit Helicopter Ride

Private Downtown Detroit Helicopter Ride

S$191
per adult
Private Downtown Detroit Helicopter Ride
Step into the shadows and discover the haunting tales of Motor City's past.

Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

S$33
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Explore Michigan Private Half-Day Walking Tour

Best Downtown Detroit Historical Walking Tour

S$134
per adult
Best Downtown Detroit Historical Walking Tour
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.

* 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.