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Windsor Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in Windsor let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Windsor in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Windsor adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Windsor with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Windsor vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Windsor Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$133
Highest Price
AU$241
Popular accommodation
Caesars Windsor, Holiday Inn Express Windsor Waterfront by IHG, Comfort Inn & Suites Ambassador Bridge, Best Western Plus Waterfront Hotel

Top trending hotels in Windsor

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is AU$241 per night from 7 Apr to 8 Apr
AU$241
includes taxes & fees
7 Apr - 8 Apr
A stay at Caesars Windsor places you in the heart of Windsor, steps from The Colosseum and a 4-minute drive from GM Renaissance Center.
Caesars Windsor
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 AU$194 per night from 20 Apr to 21 Apr
AU$194
includes taxes & fees
20 Apr - 21 Apr
With a stay at Holiday Inn Express Windsor Waterfront by IHG, you'll be centrally located in Windsor, just a 3-minute walk from Caesars Windsor and 5 minutes ...
Holiday Inn Express Windsor Waterfront by IHG
Comfort Inn & Suites Ambassador Bridge

Comfort Inn & Suites Ambassador Bridge

2.5 out of 5
2330 Huron Church Rd, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 13 Apr to 14 Apr
AU$133
includes taxes & fees
13 Apr - 14 Apr
With a stay at Comfort Inn & Suites Ambassador Bridge in Windsor (South Cameron), you'll be within a 10-minute drive of Detroit Windsor Tunnel and Caesars ...
Comfort Inn & Suites Ambassador Bridge
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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 AU$159 per night from 20 Apr to 21 Apr
AU$159
includes taxes & fees
20 Apr - 21 Apr
A stay at Best Western Plus Waterfront Hotel places you in the heart of Windsor, within a 15-minute walk of Caesars Windsor and Caesars Casino.
Best Western Plus Waterfront Hotel
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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.

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^Subject to availability and chosen travel dates.