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

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windsor holiday homes

A living room with a glass table, a potted plant, a painting, a TV, and a window with curtains.

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

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
9.0 out of 10, Wonderful, (2 reviews)
"Nice place, good location, host was nice and helpful"
United States
Abby M.
Affordable 1BHK close to Riverside, Casino, University & USA Border.
A modern living room with a sofa, coffee table, and dining area.

2. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
The price is AU$301
includes taxes & fees
15 Nov - 16 Nov
3 bdr upper, prime location
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

3. 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, (21 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is AU$258
includes taxes & fees
19 Oct - 20 Oct
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
A single-story house with a front porch, a mailbox, and a number "627" on the wall.

4. 🎰🚶‍♂️ 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 AU$356
includes taxes & fees
9 Nov - 10 Nov
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
A modern living room with a sectional sofa, a round coffee table, a flat-screen TV mounted on the wall, and a large abstract painting on the wall.

5. The Windsor Loft

The Windsor Loft
Bridgeview
The Windsor Loft
A couple in a hot tub with candles, wooden walls, and windows.

6. 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 AU$345
includes taxes & fees
10 Nov - 11 Nov
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

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
The price is AU$201
includes taxes & fees
2 Nov - 3 Nov
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
A modern living room with a grey sofa, wooden coffee table, and a dining area with a small table and chairs.

8. Cozy 2 Bedroom Luxury Suite

Cozy 2 Bedroom Luxury Suite
Roseland
10.0 out of 10, Exceptional, (1 review)
"We had a great stay! The place was very clean, comfortable, and in a great location with everything we needed nearby."
Canada
Lindsay M.
The price is AU$201
includes taxes & fees
18 Oct - 19 Oct
Cozy 2 Bedroom Luxury Suite
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

9. 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.
A spacious living room with a leather sofa, a coffee table, and a TV mounted on the wall.

10. 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 AU$469
includes taxes & fees
18 Oct - 19 Oct
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
A modern kitchen with white cabinets, stainless steel appliances, and a central island.

11. 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
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

12. 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 AU$881
includes taxes & fees
26 Oct - 27 Oct
7BR house 19 ppl DT Windsor Free Parking
A modern kitchen with a large island, stainless steel sink, and white cabinetry.

13. Cozy Modern Walkerville Basement Apartment

Cozy Modern Walkerville Basement Apartment
Walkerville
10.0 out of 10, Exceptional, (1 review)
"It was a nice clean place to spend the weekend."
United States
Robin W.
Cozy Modern Walkerville Basement Apartment
A modern living room with a sectional sofa, a coffee table, and a large window offering a view of greenery.

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 AU$341
includes taxes & fees
20 Oct - 21 Oct
Premium Stay Near Windsor Employers & Hospital
Private kitchen

15. 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
Fully Furnished 2 bedroom basement in Windsor
A modern kitchen with dark wood cabinets, stainless steel appliances, and a marble backsplash. There are two bar stools and a small island with a sink.

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 AU$476
includes taxes & fees
27 Oct - 28 Oct
Modern Spacious 1 bedroom and a den home (Lower Unit)
A staircase with a chandelier, a potted plant, and a mirror reflecting the room.

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 AU$1,418
includes taxes & fees
5 Nov - 6 Nov
Luxury getaway with pool and hot tub - family retreat
A modern dining area with a marble table, white chairs, and a vase of flowers.

18. The Windsor Mainstay

The Windsor Mainstay
Bridgeview
The Windsor Mainstay
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

19. 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, (1 review)
"Thank you for the stay, the house was amazing. Very clean quiet and family friendly! We had a great time and tired to leave the place how we found it. Thanks sm for a great stay"
United States
Tamarah M.
Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest
A neatly made bed with a white comforter and pillows, a wooden floor, and a window with dark curtains.

20. Little Belle River home

Little Belle River home
Belle River
10.0 out of 10, Exceptional, (12 reviews)
"Everything was great"
Canada
Mike
The price is AU$156
includes taxes & fees
16 Nov - 17 Nov
Little Belle River home
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

Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

8/10 Good
"This property is in a very good location in Windsor. It is right on the waterfront (great for walking and watching the ships) and very close to downtown. There is lots of parking (in the garage across the street) and the staff are consistently pleasant, professional and helpful. Some of the rooms could use some updates, especially the bathrooms but it is cleaned and well maintained."
Wendy 1-night trip
Posted 2 hours ago
Best Western Plus Waterfront Hotel

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
105
Accommodation
154 Holiday Homes
Lowest Price
AU$156
Highest Price
AU$1,418