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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday homes

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.

1. The Windsor Loft

The Windsor Loft
Bridgeview
The price is £133
includes taxes & fees
28 Sept - 29 Sept
The Windsor Loft
A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

2. 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 £128
includes taxes & fees
29 Sept - 30 Sept
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
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, (20 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is £137
includes taxes & fees
30 Sept - 1 Oct
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
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
The price is £180
includes taxes & fees
28 Sept - 29 Sept
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 £163
includes taxes & fees
29 Sept - 30 Sept
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
A living room with a glass table, a potted plant, a painting, a TV, and a window with curtains.

6. 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.
The price is £87
includes taxes & fees
22 Oct - 23 Oct
Affordable 1BHK close to Riverside, Casino, University & USA Border.
A modern kitchen with white cabinetry, a built-in microwave, and a coffee maker.

7. New 4BR Windsor Home w/ Main-Floor Ensuite & Free Parking

New 4BR Windsor Home w/ Main-Floor Ensuite & Free Parking
Ford City
9.0 out of 10, Wonderful, (9 reviews)
"Nice stay overall."
United States
Adam Y.
The price is £179
includes taxes & fees
9 Oct - 10 Oct
New 4BR Windsor Home w/ Main-Floor Ensuite & Free Parking
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

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
The price is £133
includes taxes & fees
28 Sept - 29 Sept
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
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
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 £167
includes taxes & fees
6 Oct - 7 Oct
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
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 £255
includes taxes & fees
28 Sept - 29 Sept
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
The price is £133
includes taxes & fees
1 Oct - 2 Oct
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
A modern kitchen with a large island, stainless steel sink, and white cabinetry.

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 £90
includes taxes & fees
4 Oct - 5 Oct
Cozy Modern Walkerville Basement Apartment
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.

13. 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 £256
includes taxes & fees
29 Sept - 30 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.

14. 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 £452
includes taxes & fees
13 Oct - 14 Oct
7BR house 19 ppl DT Windsor Free Parking
A staircase with a chandelier, a potted plant, and a mirror reflecting the room.

15. 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 £750
includes taxes & fees
28 Sept - 29 Sept
Luxury getaway with pool and hot tub - family retreat
A modern dining area with a marble table, white chairs, and a vase of flowers.

16. The Windsor Mainstay

The Windsor Mainstay
Bridgeview
The price is £203
includes taxes & fees
8 Oct - 9 Oct
The Windsor Mainstay
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

17. 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 £256
includes taxes & fees
28 Sept - 29 Sept
Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest

18. Modern 1BR Guesthouse | Near Marina & Golf

Modern 1BR Guesthouse | Near Marina & Golf
Windsor
9.4 out of 10, Exceptional, (3 reviews)
"To get from the driveway to the side entrance into the apartment is unsafe. There is a steep step going down from the driveway and there are no stepping stones. The apartment is lovely and we enjoyed our stay."
Canada
Maria C.
The price is £128
includes taxes & fees
1 Oct - 2 Oct
Modern 1BR Guesthouse | Near Marina & Golf
A neatly made bed with a white comforter and pillows, a wooden floor, and a window with dark curtains.

19. Little Belle River home

Little Belle River home
Belle River
10.0 out of 10, Exceptional, (11 reviews)
"My wife and I were very happy with our stay. We will definitely come back the next time we’re in the area."
Canada
GJ D.
The price is £78
includes taxes & fees
5 Oct - 6 Oct
Little Belle River home

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 £159
includes taxes & fees
28 Sept - 29 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

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

8/10 Good
"Good"
Norman 6-night trip
Posted 9 hours ago
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
97
Accommodation
154 Holiday Homes
Lowest Price
£78
Highest Price
£750