Windsor Holidays

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Our guide on 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

4 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.

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A city skyline with tall buildings and a body of water in the foreground.

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 Chrysler Theatre are top sights worth seeing.

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A historic stone building with a red roof, surrounded by trees and a Canadian flag.

Walkerville

If you're spending some time in Walkerville, Willistead Manor and Olde Walkerville Neighborhood are top sights worth seeing.

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A park with autumn foliage, a pathway, and a tall building in the background.

Bridgeview

1 out of top 10 points of interest in this area

If you're spending some time in Bridgeview, Odette Sculpture Park Walking Trail Trailhead and Ray Battagello Riverwalk Trailhead are top sights worth seeing.

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A wooden observation tower by a calm water body with tall reeds.

South Cameron

South Cameron might not have many top sights, but Mic Mac Park Walking Trails Trailhead and Comerica Park are two attractions nearby that you can check out.

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Windsor Holiday

Our pick of the best Windsor Hotel Deals

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

377 Riverside Dr E Windsor ON
NZ$134
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (3,390 reviews)
"Shower valve was broken and would jump to super hot right away and burnt me. Showed the front desk lady the video of it moving on its own and she didn’t say sorry or anything. Just oh I’ll get someone to take a look at it."

Reviewed on 27 Aug 2026

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
NZ$213
3 Sept - 4 Sept
includes taxes & fees
DoubleTree by Hilton Windsor Hotel & Suites
Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
NZ$183
6 Sept - 7 Sept
includes taxes & fees
Best Western Plus Waterfront Hotel
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

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.
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A nighttime view of a large suspension bridge with lights reflecting on the water.

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.
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A Gothic-style church with a tall tower and pointed arches.

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.
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A pedestrian walkway beside a river with a bridge in the background.

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.
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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.
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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.
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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.
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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.
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What to do in Windsor

Detroit Tigers Baseball Game at Comerica Park

Detroit Tigers Baseball Game at Comerica Park

NZ$77
per adult
Detroit Tigers Baseball Game at Comerica Park
Museum of Illusions Detroit Admission Ticket

Museum of Illusions Detroit Admission Ticket

NZ$55
per adult
100% of travellers recommend
Museum of Illusions Detroit Admission Ticket
Roasting Experience at 14th Coffee Co

Roasting Experience at 14th Coffee Co

NZ$117
per adult
Roasting Experience at 14th Coffee Co
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.