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

Windsor Vacation Rentals

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Check prices for these dates

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

Our top choices for Windsor vacation rentals

A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

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 CA $86
CA $479 total
includes taxes & fees
Sep 1 - Sep 2
Windsor Manor
A kitchen with a stainless steel refrigerator, a double sink, and a backsplash of gray tiles.

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 CA $87
CA $243 total
includes taxes & fees
Sep 3 - Sep 4
Walkerville 1BR | Parking + WiFi + Workspace
A modern living room with a flat-screen TV mounted on the wall, a glass coffee table, and a grey sofa.

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 CA $112
CA $166 total
includes taxes & fees
Sep 1 - Sep 2
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
A modern living room with a blue sofa, grey armchairs, and a glass coffee table. There are framed pictures on the wall and a window with curtains.

4. Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is CA $98
CA $299 total
includes taxes & fees
Sep 17 - Sep 18
Stylish 2bd DT Laundry and Parking
A modern living room with a fireplace, a sofa, a coffee table, and a dining 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 CA $146
CA $264 total
includes taxes & fees
Sep 8 - Sep 9
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

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 CA $94
CA $194 total
includes taxes & fees
Sep 21 - Sep 22
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
A hallway with a marble floor, a bed in the background, and a wall with circular patterns.

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

Clean and spacious 3BR DT Windsor Laundry and parking
City Centre
The price is CA $98
CA $365 total
includes taxes & fees
Aug 31 - Sep 1
Clean and spacious 3BR DT Windsor Laundry and parking

8. Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is CA $104
CA $165 total
includes taxes & fees
Sep 7 - Sep 8
Windsor Perfect Stay
A single-story house with a front porch, a mailbox, and a number "627" on the wall.

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 CA $104
CA $331 total
includes taxes & fees
Sep 23 - Sep 24
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
A modern kitchen with a central island, stainless steel appliances, and a black cabinetry design.

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 CA $131
CA $293 total
includes taxes & fees
Sep 6 - Sep 7
Historic Elegance Meets Modern Comfort|Stylish 2BR 2Bth, Walkable Heritage Area
A modern living room with a flat-screen TV, a fireplace, a round mirror, and a sofa.

11. Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
The price is CA $125
CA $258 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful gem with amazing view on the riverside
A couple in a hot tub with candles, wooden walls, and windows.

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 CA $144
CA $374 total
includes taxes & fees
Sep 27 - Sep 28
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨

13. The Windsor Loft

The Windsor Loft
Bridgeview
The price is CA $162
CA $243 total
includes taxes & fees
Aug 31 - Sep 1
The Windsor Loft
A modern living room with a sofa, coffee table, and dining area.

14. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
The price is CA $165
CA $337 total
includes taxes & fees
Sep 2 - Sep 3
3 bdr upper, prime location
A modern living room with a grey sofa, a white coffee table, and a flat-screen TV on a wooden stand.

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 CA $125
CA $173 total
includes taxes & fees
Sep 6 - Sep 7
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

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
A laundry room with stacked washers and dryers, visible pipes, and a vacuum cleaner.

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 CA $122
CA $205 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Modern Walkerville Basement Apartment
A bedroom with a bed, bedside lamps, a ceiling fan, and a window with curtains.

18. Cheerful Family Home 3 mins drive to UWindsor

Cheerful Family Home 3 mins drive to UWindsor
Bridgeview
The price is CA $96
CA $360 total
includes taxes & fees
Aug 31 - Sep 1
Cheerful Family Home 3 mins drive to UWindsor

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

Cozy 2-bedroom house in fantastic Windsor with AC
Forest Glade
The price is CA $119
CA $188 total
includes taxes & fees
Sep 28 - Sep 29
Cozy 2-bedroom house in fantastic Windsor with AC
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

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 CA $158
CA $243 total
includes taxes & fees
Aug 31 - Sep 1
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

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

10/10 Excellent
"Great location, well maintained."
Boris 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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we give you a choice of vacation rentals in Windsor close to Adventure Bay Family Water Park, or you can go with a secluded option if you want 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 vacation rentals in Windsor?

Luxury New Build 4BR Home | Modern Comfort & Style: Visitors give good reviews to this Windsor vacation home rental, which 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 vacation rentals will I find in Windsor?

With 108 Expedia vacation rentals, you're sure 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 favorite places to visit like Ford Field and Comerica Park in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are private properties you can book for short or long periods in Windsor. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips.