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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Windsor holiday homes

A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

1. 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 €125
includes taxes & fees
21 Sept - 22 Sept
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
A modern kitchen with a central island, stainless steel appliances, and a black cabinetry design.

2. Historic Elegance Meets Modern Comfort|Stylish 2BR 2Bth, Walkable Heritage Area

Historic Elegance Meets Modern Comfort|Stylish 2BR 2Bth, Walkable Heritage Area
Walkerville
Historic Elegance Meets Modern Comfort|Stylish 2BR 2Bth, Walkable Heritage Area

3. The Windsor Loft

The Windsor Loft
Bridgeview
The Windsor Loft
A modern living room with a sofa, coffee table, and dining area.

4. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
3 bdr upper, prime location
A single-story house with a front porch, a mailbox, and a number "627" on the wall.

5. 🎰🚶‍♂️ 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 €196
includes taxes & fees
3 Sept - 4 Sept
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9

6. Cozy 2-bedroom house in fantastic Windsor with AC

Cozy 2-bedroom house in fantastic Windsor with AC
Forest Glade
The price is €121
includes taxes & fees
28 Sept - 29 Sept
Cozy 2-bedroom house in fantastic Windsor with AC

7. 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 white cabinets, stainless steel appliances, and a central island.

8. 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, (11 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 €165
includes taxes & fees
1 Sept - 2 Sept
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
A couple in a hot tub with candles, wooden walls, and windows.

9. 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
10.0 out of 10, Exceptional, (1 review)
"Great stay! Walking distance to all the things in the area."
United States
Trent Y.
The price is €195
includes taxes & fees
15 Sept - 16 Sept
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
A bedroom with a large bed, wooden headboard, a nightstand, and a walk-in closet.

10. Luxury New Build 4BR Home | Modern Comfort & Style

Luxury New Build 4BR Home | Modern Comfort & Style
Ford City
8.8 out of 10, Excellent, (8 reviews)
"Everything was as describe in profile we made some amazing memories in this house and will return when we come back to visit!"
United States
Carla
The price is €176
includes taxes & fees
7 Sept - 8 Sept
Luxury New Build 4BR Home | Modern Comfort & Style
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

11. 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
The price is €155
includes taxes & fees
1 Sept - 2 Sept
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
A laundry room with stacked washers and dryers, visible pipes, and a vacuum cleaner.

12. 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.
The price is €132
includes taxes & fees
21 Sept - 22 Sept
Cozy Modern Walkerville Basement Apartment
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

13. 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, (20 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is €160
includes taxes & fees
22 Sept - 23 Sept
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
A spacious living room with a leather sofa, a coffee table, and a TV mounted on the wall.

14. 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)
"Such a cool place with loads of room but also very charming by design "
Canada
melinda
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
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.

15. 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)
"was a great property and location"
United States
Ava C.
The price is €307
includes taxes & fees
11 Sept - 12 Sept
Modern Spacious 1 bedroom and a den home (Lower Unit)
A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

16. 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 €578
includes taxes & fees
8 Sept - 9 Sept
7BR house 19 ppl DT Windsor Free Parking

17. The Windsor Mainstay

The Windsor Mainstay
Bridgeview
The Windsor Mainstay
A staircase with a chandelier, a potted plant, and a mirror reflecting the room.

18. 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)
"We didn’t get bothered at all but parking was tight and should let guest know there are people downstairs "
Canada
Matthew K.
The price is €875
includes taxes & fees
1 Sept - 2 Sept
Luxury getaway with pool and hot tub - family retreat
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.
The price is €298
includes taxes & fees
1 Sept - 2 Sept
Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest

20. Spacious 3BR Basement Suite | Near 5min Gordie Howe Bridge | Families & Groups

Spacious 3BR Basement Suite | Near 5min Gordie Howe Bridge | Families & Groups
Windsor
The price is €185
includes taxes & fees
1 Sept - 2 Sept
Spacious 3BR Basement Suite | Near 5min Gordie Howe Bridge | Families & Groups
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

Comfort Inn & Suites Ambassador Bridge

Comfort Inn & Suites Ambassador Bridge

8/10 Good
"Clean room, beds firm and comfortable, the breakfast room very small. Not enough tables to accommodate everyone and difficult to maneuver around for the food. Coffee is horrible."
Donicka 1-night trip
Posted 4 hours ago
Comfort Inn & Suites Ambassador Bridge

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
75
Accommodation
154 Holiday Homes
Lowest Price
€121
Highest Price
€875