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

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor holiday rentals

Living room

1. Windsor Manor

Windsor Manor
4.0 star property
City Centre
10.0 out of 10, Exceptional, (2 reviews)
"Facility was spotless. There were no staff members on site"
Canada
Jacob
The price is HK$480
HK$2,369 total
includes taxes & fees
2 Sept - 3 Sept
Windsor Manor
Private kitchen

2. Walkerville 1BR | Parking + WiFi + Workspace

Walkerville 1BR | Parking + WiFi + Workspace
Walkerville
10.0 out of 10, Exceptional, (1 review)
"Wonderful property with all amenities provided . The neighborhood is equally nice and safe."
Canada
harchetan
The price is HK$492
HK$1,371 total
includes taxes & fees
3 Sept - 4 Sept
Walkerville 1BR | Parking + WiFi + Workspace
Room

3. 6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
East Windsor
9.4 out of 10, Exceptional, (6 reviews)
"Amazing stay, Very clean and nice inside. Host is also nice and easy to communicate with."
Canada
Kruz
The price is HK$632
HK$935 total
includes taxes & fees
1 Sept - 2 Sept
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
Interior

4. Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is HK$540
HK$1,703 total
includes taxes & fees
17 Sept - 18 Sept
Stylish 2bd DT Laundry and Parking
Living area

5. Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
City Centre
10.0 out of 10, Exceptional, (11 reviews)
"We loved our quick stay at Casa Rio - cute, comfortable, and equipped with anything we needed, very close to the river walk, just blocks from the casino, fun restaurants and bars. Great experience - will come back again!"
United States
Stacy A.
The price is HK$792
HK$1,462 total
includes taxes & fees
9 Sept - 10 Sept
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
Interior

6. 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 HK$536
HK$1,102 total
includes taxes & fees
29 Sept - 30 Sept
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Interior

7. Clean and spacious 3BR DT Windsor Laundry and parking

Clean and spacious 3BR DT Windsor Laundry and parking
City Centre
The price is HK$785
HK$2,385 total
includes taxes & fees
30 Sept - 1 Oct
Clean and spacious 3BR DT Windsor Laundry and parking
Private kitchen

8. Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is HK$648
HK$1,000 total
includes taxes & fees
30 Sept - 1 Oct
Windsor Perfect Stay
Exterior detail

9. 🎰🚶‍♂️ 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$426
HK$1,670 total
includes taxes & fees
2 Sept - 3 Sept
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Private kitchen

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

Historic Elegance Meets Modern Comfort|Stylish 2BR 2Bth, Walkable Heritage Area
Walkerville
The price is HK$736
HK$1,666 total
includes taxes & fees
6 Sept - 7 Sept
Historic Elegance Meets Modern Comfort|Stylish 2BR 2Bth, Walkable Heritage Area
Living area

11. Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
The price is HK$705
HK$1,459 total
includes taxes & fees
1 Sept - 2 Sept
Beautiful gem with amazing view on the riverside
Spa

12. 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 HK$533
HK$1,781 total
includes taxes & fees
15 Sept - 16 Sept
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
Living area

13. The Windsor Loft

The Windsor Loft
Bridgeview
The price is HK$913
HK$1,370 total
includes taxes & fees
13 Sept - 14 Sept
The Windsor Loft
Interior

14. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
The price is HK$930
HK$1,931 total
includes taxes & fees
13 Sept - 14 Sept
3 bdr upper, prime location
Living area

15. Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Walkerville
9.0 out of 10, Wonderful, (2 reviews)
"Very clean, beautiful home, and the host, Yolanda, is amazing with communication:)"
United States
Mary M.
The price is HK$784
HK$1,064 total
includes taxes & fees
31 Aug - 1 Sept
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Private kitchen

16. 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
Interior

17. 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 HK$685
HK$1,158 total
includes taxes & fees
21 Sept - 22 Sept
Cozy Modern Walkerville Basement Apartment
Room

18. Cheerful Family Home 3 mins drive to UWindsor

Cheerful Family Home 3 mins drive to UWindsor
Bridgeview
Cheerful Family Home 3 mins drive to UWindsor
Pool

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

Cozy 2-bedroom house in fantastic Windsor with AC
Forest Glade
The price is HK$670
HK$1,063 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 2-bedroom house in fantastic Windsor with AC
Interior

20. 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 HK$891
HK$1,373 total
includes taxes & fees
13 Sept - 14 Sept
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
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

TownePlace Suites by Marriott Windsor

TownePlace Suites by Marriott Windsor

10/10 Excellent
"Very clean and easy check in! Great location, very centrally located. Good value for price. Breakfast was a nice bonus!"
stephy 2-night trip
Posted less than an hour ago
TownePlace Suites by Marriott Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Adventure Bay Family Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windsor speak positively about the scenic riverfront and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best holiday rentals that Windsor has to offer?

Luxury New Build 4BR Home | Modern Comfort & Style: This highly rated holiday home rental in Windsor offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden. Some other homes for rent in Windsor include 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9 and Paradise Home - Your Home Away From Home.

How many holiday rentals will I find in Windsor?

With 108 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What’s there to see and do in Windsor?

Family-friendly attractions include Adventure Bay Family Water Park and Olde Walkerville Neighborhood, whereas Windsor Riverfront and Lake Saint Clair are a couple of great spots to enjoy the outdoors. You’ll find favourite places to visit such as Ford Field and Comerica Park in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.