Windsor Trips (flight + hotel)

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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

4 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

Top hotels in Windsor

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is P5,998 per night from Sep 1 to Sep 2
P5,998
P8,222 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (3,038 reviews)
"The staff was great. Our concert got done and Johnny Rockets had about 30 minutes til closing and only turned 1 person away at 12:00 am. We honestly thought that we would have to eat at Tim Hortons, and the food was AMAZING! We stayed in the forum tower and we really thought for the price of the ..."

Reviewed on Aug 10, 2025

Caesars 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 P6,772 per night from Aug 13 to Aug 14
P6,772
P8,112 total
Aug 13 - Aug 14
includes taxes & fees
8/10 Very Good! (1,007 reviews)
"Good location. Few inconveniences as the pool was under Reno’s and no microwave in the room which we didn’t plan for. But it was clean."

Reviewed on Aug 8, 2025

Best Western Plus Waterfront Hotel
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 P5,436 per night from Aug 17 to Aug 18
P5,436
P6,511 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,282 reviews)
"Absolutely enjoyed our stay. Friendly staff, clean place. Was there only for a night and had a comfortable stay."

Reviewed on Aug 8, 2025

Holiday Inn Express Windsor Waterfront by IHG
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.

Popular places to visit

Windsor Riverfront

Windsor Riverfront

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

Windsor Riverfront

Windsor Family Credit Union Centre

Catch an event at Windsor Family Credit Union Centre during your trip to Windsor. Stroll along the riverfront or experience the great live music in this vibrant area.

Windsor Family Credit Union Centre

What to do in Windsor

Step into the shadows and discover the haunting tales of Motor City's past.

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

P1,512
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Detroit Flavors Food Tour

Detroit Flavors Food Tour

P8,725
per adult
Detroit Flavors Food Tour
Sunset Helicopter Experience in Downtown Detroit

Sunset Helicopter Experience in Downtown Detroit

P10,179
per adult
Sunset Helicopter Experience in Downtown Detroit
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation 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 vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation 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 vacation, we suggest staying for 2 days. Split your time between discovering Chrysler Theatre, Walkerville Brewery and other well-known attractions, as well as experiencing neighborhoods like East Windsor and Walkerville. If you've got some time to spare, include a day trip in your Windsor vacation itinerary.
Is it worth booking a vacation package to Windsor?
Windsor offers everything you need for an unforgettable getaway. Get your Windsor vacation 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 personalize 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 vacation as a package?
Expedia vacation 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 customized Windsor vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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 accommodations 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 vacation 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.