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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windsor holiday rentals

Lobby sitting area

1. Residence & Conference Centre - Windsor

Residence & Conference Centre - Windsor
2.0 star property
Roseland
8.4 out of 10, Very good, (485 reviews)
"quiet clean comfy beds great stay with my family highly recommend"
Canada
mark
The price is NZ$95
includes taxes & fees
13 Aug - 14 Aug
Residence & Conference Centre - Windsor
Smart TV

2. 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 NZ$508
includes taxes & fees
10 Sept - 11 Sept
Windsor Manor
Coffee/tea maker, fridge, microwave, oven

3. Walkerville 1BR Apartment | WiFi + Workspace

Walkerville 1BR Apartment | WiFi + Workspace
Walkerville
The price is NZ$271
includes taxes & fees
18 Aug - 19 Aug
Walkerville 1BR Apartment | WiFi + Workspace
Interior

4. Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is NZ$201
includes taxes & fees
19 Aug - 20 Aug
Windsor Perfect Stay
Interior

5. 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 NZ$237
includes taxes & fees
17 Aug - 18 Aug
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Interior

6. Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is NZ$359
includes taxes & fees
17 Aug - 18 Aug
Stylish 2bd DT Laundry and Parking
Interior

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

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
The price is NZ$174
includes taxes & fees
18 Aug - 19 Aug
Affordable 1BHK close to Riverside, Casino, University & USA Border.
1 bedroom, desk, iron/ironing board, free WiFi

8. 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
9.6 out of 10, Exceptional, (5 reviews)
"Amazing stay, Very clean and nice inside. Host is also nice and easy to communicate with."
Canada
Kruz
The price is NZ$199
includes taxes & fees
10 Sept - 11 Sept
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
Living area

9. Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
The price is NZ$315
includes taxes & fees
24 Aug - 25 Aug
Beautiful gem with amazing view on the riverside
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy 2-bedroom house in fantastic Windsor with AC
Forest Glade
The price is NZ$203
includes taxes & fees
20 Aug - 21 Aug
Cozy 2-bedroom house in fantastic Windsor with AC
Interior

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

Clean and spacious 3BR DT Windsor Laundry and parking
City Centre
The price is NZ$474
includes taxes & fees
17 Aug - 18 Aug
Clean and spacious 3BR DT Windsor Laundry and parking
Smart TV

12. 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 NZ$315
includes taxes & fees
17 Aug - 18 Aug
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
Interior

13. 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 NZ$297
includes taxes & fees
13 Aug - 14 Aug
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
Exterior detail

14. 🎰🚶‍♂️ 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)
"It was great, very short walk to the casino!"
United States
tiara t.
The price is NZ$384
includes taxes & fees
8 Sept - 9 Sept
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Iron/ironing board, WiFi

15. 3 Bedrooms, 2 Kitchens & 2 Bathrooms—Perfect for Groups

3 Bedrooms, 2 Kitchens & 2 Bathrooms—Perfect for Groups
Walkerville
The price is NZ$546
includes taxes & fees
16 Aug - 17 Aug
3 Bedrooms, 2 Kitchens & 2 Bathrooms—Perfect for Groups
Dining

16. The Windsor Mainstay

The Windsor Mainstay
Bridgeview
The price is NZ$472
includes taxes & fees
13 Aug - 14 Aug
The Windsor Mainstay
Coffee/tea maker, fridge, microwave, oven

17. 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 NZ$255
includes taxes & fees
13 Aug - 14 Aug
Fully Furnished 2 bedroom basement in Windsor
TV

18. 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 NZ$230
includes taxes & fees
24 Aug - 25 Aug
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Spa

19. 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 NZ$389
includes taxes & fees
7 Sept - 8 Sept
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
Fridge, microwave, oven, stovetop

20. 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 NZ$316
includes taxes & fees
22 Aug - 23 Aug
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
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

10/10 Excellent
"16 yr old could not use pool or gym"
Dwayne 1-night trip
Posted less than an hour ago
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Find out more about Windsor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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 can relax into your holiday with a garden and 1 hot tub. 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 107 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 Dieppe Gardens, whereas Windsor Riverfront and Mic Mac Park Walking Trails Trailhead 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.