Book Holiday Homes in Windsor

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Windsor

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 15 Apr to 16 Apr
AU$462
per night
15 Apr - 16 Apr
With a stay at this vacation home in Kingsville, you'll be a 4-minute walk from Lake Erie and within a 5-minute drive of Lakeside Park Walking Paths ...
The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca
Luxurious & spacious 3 bedroom home in Windsor.

Luxurious & spacious 3 bedroom home in Windsor.

Windsor
With a stay at this vacation home in Windsor, you'll be within a 15-minute drive of Caesars Windsor and Detroit Windsor Tunnel.
Luxurious & spacious 3 bedroom home in Windsor.
Windsor's Versace House 10min to all downtown adventures & beautiful river walks

Windsor's Versace House 10min to all downtown adventures & beautiful river walks

Windsor
With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of Detroit Windsor Tunnel and Caesars Windsor.
Windsor's Versace House 10min to all downtown adventures & beautiful river walks
Save an average of 15% on thousands of hotels when you're signed in
3 Bedroom basement unit with Free Parking , WiFi.

3 Bedroom basement unit with Free Parking , WiFi.

Windsor
With a stay at this vacation home in LaSalle, you'll be within a 15-minute drive of Ambassador Golf Club and University of Windsor.
3 Bedroom basement unit with Free Parking , WiFi.
Full House - 5 Bed, 2 Bath

Full House - 5 Bed, 2 Bath

Windsor
With a stay at this vacation home in Windsor, you'll be within a 15-minute drive of Caesars Windsor and Detroit Windsor Tunnel.
Full House - 5 Bed, 2 Bath
Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach

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

Harrow
With a stay at this vacation home in Town of Essex, you'll be on a lake, within a 10-minute drive of Lake Erie and North 42 Degrees Estate Winery.
Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach
VICTORIA HOUSE

VICTORIA HOUSE

Windsor
With a stay at this vacation home, you'll be centrally located in Windsor, within a 5-minute drive of Detroit Windsor Tunnel and Caesars Windsor.
VICTORIA HOUSE
CREEKSIDE COTTAGE - Waterfront Retreat

CREEKSIDE COTTAGE - Waterfront Retreat

Kingsville
With a stay at this vacation home in Kingsville, you'll be on the waterfront, just a 5-minute walk from Lake Erie and within a 5-minute drive of Lakeside Park ...
CREEKSIDE COTTAGE - Waterfront Retreat
Full house - 5 bed, 2 bath

Full house - 5 bed, 2 bath

Windsor
The price is AU$369 per night from 12 Apr to 13 Apr
AU$369
per night
12 Apr - 13 Apr
With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of Caesars Windsor and Detroit Windsor Tunnel.
Full house - 5 bed, 2 bath
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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
93 Holiday Homes
Lowest Price
AU$185
Highest Price
AU$462
Popular accommodation
The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca, Luxurious & spacious 3 bedroom home in Windsor., Windsor's Versace House 10min to all downtown adventures & beautiful river walks, 3 Bedroom basement unit with Free Parking , WiFi., Full House - 5 Bed, 2 Bath, Peaceful Lakefront Cottage~Clean & Comfortable, BBQ, FirePit, nr wineries beach, VICTORIA HOUSE, CREEKSIDE COTTAGE - Waterfront Retreat, Full house - 5 bed, 2 bath

Top trending hotels in Windsor

Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is AU$202 per night from 31 Mar to 1 Apr
AU$202
per night
31 Mar - 1 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, an IHG Hotel

Holiday Inn Express Windsor Waterfront, an IHG Hotel

2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
The price is AU$196 per night from 31 Mar to 1 Apr
AU$196
per night
31 Mar - 1 Apr
With a stay at Holiday Inn Express Windsor Waterfront, an IHG Hotel, you'll be centrally located in Windsor, just a 3-minute walk from Caesars Windsor and 5 ...
Holiday Inn Express Windsor Waterfront, an IHG Hotel
Stonecroft Inn

Stonecroft Inn

3 out of 5
3032 Dougall Ave, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 1 Apr to 2 Apr
AU$185
per night
1 Apr - 2 Apr
When you stay at Stonecroft Inn in Windsor, you'll be near the airport, within a 5-minute drive of Devonshire Mall and St. Clair College.
Stonecroft Inn
Save an average of 15% on thousands of hotels when you're signed in
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$203 per night from 16 Apr to 17 Apr
AU$203
per night
16 Apr - 17 Apr
With a stay at DoubleTree by Hilton Windsor Hotel & Suites in Windsor, you'll be within a 15-minute walk of Caesars Casino and Detroit Windsor Tunnel.
DoubleTree by Hilton Windsor Hotel & Suites
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.