A city skyline with a prominent casino building, a tall skyscraper, and several other high-rise buildings along a waterfront.

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Our top choices for Windsor holiday homes

1. Affordable 1BHK close to Riverside, Casino, University & USA Border.

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
9.6 out of 10, Exceptional, (4 reviews)
"Great location, spacious."
Canada
Laurie
The price is HK$479
HK$858 total
includes taxes & fees
1 Dec - 2 Dec
Affordable 1BHK close to Riverside, Casino, University & USA Border.

2. Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
South Windsor
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is HK$765
HK$1,313 total
includes taxes & fees
18 Nov - 19 Nov
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

3. 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9

🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Walkerville
8.8 out of 10, Excellent, (20 reviews)
"Great communication with host, clean, convenient parking and excellent location for events at Caesars!"
United States
Valerie C.
The price is HK$659
HK$1,853 total
includes taxes & fees
15 Nov - 16 Nov
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9

4. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
3 bdr upper, prime location

5. Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨

Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
City Centre
9.0 out of 10, Wonderful, (2 reviews)
"Great stay! Walking distance to all the things in the area."
United States
Trent Y.
The price is HK$753
HK$1,908 total
includes taxes & fees
10 Dec - 11 Dec
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨

6. Cozy Modern Walkerville Basement Apartment

Cozy Modern Walkerville Basement Apartment
Walkerville
10.0 out of 10, Exceptional, (2 reviews)
"It was a nice clean place to spend the weekend."
United States
Robin W.
The price is HK$481
HK$837 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Modern Walkerville Basement Apartment

7. Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit

Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Bridgeview
10.0 out of 10, Exceptional, (1 review)
"Nicely decorated with all the required items. Great location on the river with awesome views and great sunsets "
Canada
John P.
The price is HK$517
HK$1,001 total
includes taxes & fees
15 Nov - 16 Nov
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit

8. Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.

Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
Devonshire
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay. The host was very responsive and addressed any issues quickly. The property was very clean, and the location was very convenient. Would definitely stay again."
Canada
Junwu
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.

9. Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !

Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
Walkerville
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place to stay. Great location....perfect for two couples. Nice space indoors and outdoors."
United States
Nicole C.
The price is HK$1,514
HK$2,448 total
includes taxes & fees
13 Nov - 14 Nov
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !

10. Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Devonshire
9.0 out of 10, Wonderful, (12 reviews)
"Home was very clean, good location close to major amenities, Devonshire mall, Costco. Easy access via key pad, ample parking. "
Canada
Tony
The price is HK$870
HK$1,272 total
includes taxes & fees
13 Nov - 14 Nov
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

11. 7BR house 19 ppl DT Windsor Free Parking

7BR house 19 ppl DT Windsor Free Parking
City Centre
4.0 out of 10, (1 review)
"The main floor refrigerator didn’t work and the roof leaked when it rained all over the master bed through the ceiling fan."
United States
Mark D.
The price is HK$1,428
HK$4,400 total
includes taxes & fees
18 Nov - 19 Nov
7BR house 19 ppl DT Windsor Free Parking

12. Fully Furnished 2 bedroom basement in Windsor

Fully Furnished 2 bedroom basement in Windsor
Walkerville
4.8 out of 10, (3 reviews)
"The home owner was incredibly nice and accommodating. They even picked us up from the train station nearby, and answered any msg quickly. I really appreciated that. Great neighborhood. The actual apartment wasn't quite what was advertised, the place wasn't as classy as the vrbo pictures. Also i thought vrbo was all about having a place to yourself? I was woken up a few times by footsteps upstairs where the owner lives. No laundry detergent, no bbq, 1 1/2 rolls of tp provided. Not worth the cost...
Canada
Kirk
The price is HK$590
HK$1,015 total
includes taxes & fees
18 Nov - 19 Nov
Fully Furnished 2 bedroom basement in Windsor

13. Spacious 5-Bedroom Home in Central Windsor,ON – Near USA Border,

Spacious 5-Bedroom Home in Central Windsor,ON – Near USA Border,
East Windsor
The price is HK$1,080
HK$1,712 total
includes taxes & fees
18 Nov - 19 Nov
Spacious 5-Bedroom Home in Central Windsor,ON – Near USA Border,

14. Premium Stay Near Windsor Employers & Hospital

Premium Stay Near Windsor Employers & Hospital
Ford City
9.0 out of 10, Wonderful, (11 reviews)
"Nice stay overall."
United States
Adam Y.
The price is HK$892
HK$1,723 total
includes taxes & fees
18 Nov - 19 Nov
Premium Stay Near Windsor Employers & Hospital

15. The Windsor Mainstay

The Windsor Mainstay
Bridgeview
10.0 out of 10, Exceptional, (1 review)
"Overall happy with the unitClose to activities we rented for water Park.Being close to train and moving of cars around at 2 am was disruptive."
United States
rose h.
The price is HK$1,387
HK$1,947 total
includes taxes & fees
18 Nov - 19 Nov
The Windsor Mainstay

16. Modern Spacious 1 bedroom and a den home (Lower Unit)

Modern Spacious 1 bedroom and a den home (Lower Unit)
Roseland
8.0 out of 10, Very good, (9 reviews)
"Very clean and everything that we thought it would be from the pictures"
United States
Dannavan C.
The price is HK$743
HK$1,910 total
includes taxes & fees
18 Nov - 19 Nov
Modern Spacious 1 bedroom and a den home (Lower Unit)

17. Luxury getaway with pool and hot tub - family retreat

Luxury getaway with pool and hot tub - family retreat
Roseland
7.2 out of 10, Good, (5 reviews)
"Clean and gorgeous backyard with heated pool and jacuzzi"
United States
Mohammed M.
The price is HK$1,376
HK$4,006 total
includes taxes & fees
13 Nov - 14 Nov
Luxury getaway with pool and hot tub - family retreat

18. Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest

Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest
Devonshire
10.0 out of 10, Exceptional, (2 reviews)
"Spacious, clean, and thoughtful amenities provided. Appreciated the closeness to the border as we were coming back from the US late in the evening."
Canada
Pauline
The price is HK$1,762
HK$2,589 total
includes taxes & fees
13 Dec - 14 Dec
Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest

19. Executive One-Bedroom Upper Unit

Executive One-Bedroom Upper Unit
Windsor
9.0 out of 10, Wonderful, (7 reviews)
"Property was as described. Very comfortable and in good condition. Excellent value."
Canada
Mary
The price is HK$524
HK$1,009 total
includes taxes & fees
29 Nov - 30 Nov
Executive One-Bedroom Upper Unit

20. 14th Coffee Co. Homestead Farmhouse

14th Coffee Co. Homestead Farmhouse
Essex
9.6 out of 10, Exceptional, (9 reviews)
"House was excellent!!! The only issue we experienced was the hot tub, it was so so strong with chlorine we couldn’t stay in it, ever our swim clothes got bleached."
Canada
Pete
The price is HK$1,120
HK$1,703 total
includes taxes & fees
23 Nov - 24 Nov
14th Coffee Co. Homestead Farmhouse
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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Top Windsor Hotel Reviews

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
113
Accommodation
155 Vacation Homes
Lowest Price
HK$837
Highest Price
HK$4,400