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 NZ$423 per night from 30 Apr to 1 May
NZ$423
includes taxes & fees
30 Apr - 1 May
Stay at this vacation home in Kingsville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Cedar Island Beach and Chrysler Greenway are ...
Wild Goose Landing- Located near local wineries and breweries
Fully Furnished 2 bedroom house in Windsor

Fully Furnished 2 bedroom house in Windsor

Windsor
Stay at this vacation home in Windsor. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Ford Field and MGM Grand Detroit 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 NZ$577 per night from 13 May to 14 May
NZ$577
includes taxes & fees
13 May - 14 May
Stay at this vacation home in Windsor. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions MGM Grand Detroit Casino and Ford Field are ...
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 NZ$492 per night from 30 Apr to 1 May
NZ$492
includes taxes & fees
30 Apr - 1 May
Stay at this vacation home in Kingsville. Enjoy free WiFi, a garden, and patios. Popular attractions Cedar Island Beach and Chrysler Greenway are located ...
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
Stay at this vacation home in Kingsville. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Pelee Island Winery and Lakeside ...
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
Stay at this vacation home in Town of Essex. Enjoy free WiFi, a garden, and patios. Popular attractions Oxley Estate Winery and Cooper's Hawk Vineyards are located ...
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
Stay at this vacation home in Lakeshore. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning.
Amazing 3 bedroom on Lake St.Clair all amenities Lakeview Dr. Belle River
The Hipster House

The Hipster House

Windsor
Stay at this vacation home in Windsor. Enjoy air conditioning. Popular attractions Ford Field and MGM Grand Detroit Casino are located nearby.
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
Stay at this vacation home in Town of Essex. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Erie Shore Vineyard and Colchester Beach ...
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
NZ$165
Highest Price
NZ$577
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 NZ$251 per night from 12 May to 13 May
NZ$251
includes taxes & fees
12 May - 13 May
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
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$165 per night from 4 May to 5 May
NZ$165
includes taxes & fees
4 May - 5 May
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
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$239 per night from 18 May to 19 May
NZ$239
includes taxes & fees
18 May - 19 May
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
Save an average of 15% on thousands of hotels when you're signed in
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$207 per night from 4 May to 5 May
NZ$207
includes taxes & fees
4 May - 5 May
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
Don't see what you're looking for?
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.

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^Subject to availability and chosen travel dates.