Book Holiday Homes in Windsor

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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
NZ$171
Highest Price
NZ$260
Popular accommodation
Caesars Windsor, DoubleTree by Hilton Windsor Hotel & Suites, Holiday Inn Express Windsor Waterfront by IHG, 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 NZ$260 per night from 8 Apr to 9 Apr
NZ$260
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and 6 restaurants. Our guests praise the bar and the helpful staff in ...
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 NZ$248 per night from 20 Apr to 21 Apr
NZ$248
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
DoubleTree by Hilton Windsor Hotel & Suites
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 NZ$209 per night from 20 Apr to 21 Apr
NZ$209
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Holiday Inn Express Windsor Waterfront by IHG
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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 NZ$171 per night from 20 Apr to 21 Apr
NZ$171
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Windsor. Enjoy breakfast (surcharge), a fitness center, and parking (surcharge). Our guests praise the helpful ...
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.