Book Holiday Homes in Windsor

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Featured Holiday Homes in Windsor

Wild Goose Landing- Located near local wineries and breweries

Wild Goose Landing- Located near local wineries and breweries

Kingsville
The price is AU$397 per night from 30 Apr to 1 May
AU$397
includes taxes & fees
30 Apr - 1 May
When you stay at this vacation home in Kingsville, you'll be on the waterfront, just steps from Lake Erie and a 3-minute drive from Cedar Island Beach.
Wild Goose Landing- Located near local wineries and breweries
Fully Furnished 2 bedroom house in Windsor

Fully Furnished 2 bedroom house in Windsor

Windsor
With a stay at this vacation home in Windsor (Walkerville), you'll be within a 5-minute drive of Caesars Windsor and Caesars Casino.
Fully Furnished 2 bedroom house in Windsor
Min to DT/USA - Luxurious House - 4bed-2bath

Min to DT/USA - Luxurious House - 4bed-2bath

Windsor
The price is AU$405 per night from 30 Apr to 1 May
AU$405
includes taxes & fees
30 Apr - 1 May
With a stay at this vacation home in Windsor (Bridgeview), you'll be within a 5-minute drive of Detroit Windsor Tunnel and Caesars Windsor.
Min to DT/USA - Luxurious House - 4bed-2bath
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The Cedar House. Minutes from the lake, wineries and golf.  www.thecedarhouse.ca

The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca

Kingsville
The price is AU$462 per night from 30 Apr to 1 May
AU$462
includes taxes & fees
30 Apr - 1 May
With a stay at this vacation home in Kingsville, you'll be a 4-minute walk from Lake Erie and 13 minutes by foot from Cedar Island Beach.
The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca
Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home in Kingsville

Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home in Kingsville

Kingsville
When you stay at this vacation home in Kingsville, you'll be on the waterfront, just steps from Lake Erie and a 3-minute drive from Pelee Island Winery.
Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home in Kingsville
Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach

Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach

Harrow
When you stay at this vacation home in Town of Essex, you'll be on a lake, just steps from Lake Erie and a 4-minute drive from Oxley Estate Winery.
Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach
Amazing 3 bedroom on Lake St.Clair all amenities Lakeview Dr. Belle River

Amazing 3 bedroom on Lake St.Clair all amenities Lakeview Dr. Belle River

Belle River
When you stay at this vacation home in Lakeshore, you'll be 12 minutes by foot from Lake Saint Clair.
Amazing 3 bedroom on Lake St.Clair all amenities Lakeview Dr. Belle River
The Hipster House

The Hipster House

Windsor
With a stay at this vacation home in Windsor (Walkerville), you'll be within a 5-minute drive of Caesars Windsor and Caesars Casino.
The Hipster House
Beautiful Waterfront Lake House in the Heart of Epic Wine Country

Beautiful Waterfront Lake House in the Heart of Epic Wine Country

Essex
With a stay at this vacation home in Town of Essex (Essex), you'll be steps from Lake Erie and a 3-minute drive from Erie Shore Vineyard.
Beautiful Waterfront Lake House in the Heart of Epic Wine Country
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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.

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
166 Holiday Homes
Lowest Price
AU$153
Highest Price
AU$462
Popular accommodation
Wild Goose Landing- Located near local wineries and breweries, Fully Furnished 2 bedroom house in Windsor, Min to DT/USA - Luxurious House - 4bed-2bath, The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca, Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home in Kingsville, Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach, Amazing 3 bedroom on Lake St.Clair all amenities Lakeview Dr. Belle River, The Hipster House , Beautiful Waterfront Lake House in the Heart of Epic Wine Country

Top trending hotels in Windsor

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is AU$233 per night from 12 May to 13 May
AU$233
includes taxes & fees
12 May - 13 May
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
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$153 per night from 4 May to 5 May
AU$153
includes taxes & fees
4 May - 5 May
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
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 AU$222 per night from 25 May to 26 May
AU$222
includes taxes & fees
25 May - 26 May
With a stay at DoubleTree by Hilton Windsor Hotel & Suites in Windsor (City Centre), you'll be within a 15-minute walk of Caesars Casino and Detroit Windsor ...
DoubleTree by Hilton Windsor Hotel & Suites
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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$205 per night from 18 May to 19 May
AU$205
includes taxes & fees
18 May - 19 May
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
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See all available properties in Windsor
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.