Windsor Packages (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
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 The Colosseum at Caesars Windsor.
Walkerville
If you're spending some time in Walkerville, Willistead Manor and Olde Walkerville Neighborhood are top sights worth seeing.
City Centre
2 out of top 10 points of interest in this area
If you're spending some time in City Centre, Detroit Windsor Tunnel and The Colosseum at Caesars Windsor are top sights worth seeing.
Bridgeview
1 out of top 10 points of interest in this area
If you're spending some time in Bridgeview, University of Windsor Stadium and Roy A. Battagello Riverwalk Trailhead are top sights worth seeing.
South Cameron
South Cameron might not have many top sights, but REVS Rose Bowl and Ford Field are two attractions nearby that you can check out.
Top hotels in Windsor
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
377 Riverside Dr E Windsor ON
฿1,679
฿2,602 total
14 Oct - 15 Oct
includes taxes & fees
8.8/10 Excellent! (3,548 reviews)
"The hotel was inviting and well maintained. The rooms were clean and spacious. The food choices were really great as well. However, the walk from the garage to the check-in desk was extremely long and confusing upon arrival."
Reviewed on 6 Oct 2026
Best Western Plus Waterfront Hotel
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
฿3,163
฿3,788 total
12 Oct - 13 Oct
includes taxes & fees
8.4/10 Very good! (1,324 reviews)
"The staff was professional and nice."
Reviewed on 6 Oct 2026
Holiday Inn Express Windsor Waterfront by IHG
33 Riverside Drive East Windsor ON
Fully refundable
฿3,391
฿4,062 total
1 Nov - 2 Nov
includes taxes & fees
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
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.
Ambassador Bridge
8.2/10 (577 reviews)
This iconic international suspension bridge carries 25% of all US-Canada trade across the Detroit River. Travellers enjoy spectacular views of both Detroit and Windsor skylines during the brief but memorable crossing.
University of Windsor
8.0/10 (526 reviews)
This riverside campus blends historic architecture with modern facilities along the Detroit River. Explore public lectures, art exhibitions, and cultural events year-round at this comprehensive Canadian university.
Windsor Riverfront
10.0/10 (2 reviews)
Windsor Riverfront offers panoramic views of Detroit's skyline alongside a collection of contemporary sculptures. Stroll the waterfront trail at sunset or enjoy seasonal festivals in this urban oasis.
Detroit Windsor Tunnel
8.0/10 (1,568 reviews)
This underwater crossing connects Detroit, Michigan to Windsor, Ontario beneath the Detroit River. Experience a seamless border transition through one of the few subaquatic international tunnels in the world.
Adventure Bay Family Water Park
7.6/10 (164 reviews)
Adventure Bay Family Water Park offers 35,000 square feet of aquatic thrills including water slides, a wave pool, and a FlowRider surf simulator. Visit weekday mornings for shorter wait times at this Windsor attraction.
Devonshire Mall
8.4/10 (475 reviews)
Windsor's largest shopping destination houses over 168 stores and a 12-screen Cineplex Odeon. Browse major retailers, refuel at the diverse food court, or catch a film for a complete retail experience.
The Colosseum at Caesars Windsor
8.0/10 (257 reviews)
This premier venue within Caesars Windsor offers intimate seating and perfect acoustics for world-class performances. Arrive early to enjoy dinner before experiencing the show's electric atmosphere.
What to do in Windsor
Macabre, Murder, & Mayhem in Motor City : Detroit Ghost Tour
฿868
per adult
Best Detroit Architecture Walking Tour: Inside Access & Landmarks
฿4,340
per adult
100% of travellers recommend
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?
- 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.
- 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.
- 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.
- 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.
