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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 $81
CA $420 total
includes taxes & fees
Oct 13 - Oct 14
Windsor Manor
A living room with a glass table, a potted plant, a painting, a TV, and a window with curtains.

2. 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 CA $79
CA $155 total
includes taxes & fees
Oct 26 - Oct 27
Affordable 1BHK close to Riverside, Casino, University & USA Border.
A hallway with a marble floor, a bed in the background, and a wall with circular patterns.

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

Clean and spacious 3BR DT Windsor Laundry and parking
City Centre
The price is CA $102
CA $332 total
includes taxes & fees
Oct 13 - Oct 14
Clean and spacious 3BR DT Windsor Laundry and parking
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.

4. The Windsor Loft

The Windsor Loft
Bridgeview
The price is CA $162
CA $244 total
includes taxes & fees
Oct 5 - Oct 6
The Windsor Loft
A modern living room with a flat-screen TV mounted on the wall, a glass coffee table, and a grey sofa.

5. 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 $110
CA $165 total
includes taxes & fees
Oct 5 - Oct 6
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

6. 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 CA $139
CA $252 total
includes taxes & fees
Oct 5 - Oct 6
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
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.

7. Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is CA $83
CA $281 total
includes taxes & fees
Oct 7 - Oct 8
Stylish 2bd DT Laundry and Parking
A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

8. 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 $195 total
includes taxes & fees
Nov 1 - Nov 2
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
A modern living room with a fireplace, a sofa, a coffee table, and a dining area.

9. 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, (12 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 $126
CA $243 total
includes taxes & fees
Nov 2 - Nov 3
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
A couple in a hot tub with candles, wooden walls, and windows.

10. 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 CA $116
CA $337 total
includes taxes & fees
Nov 2 - Nov 3
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
A single-story house with a front porch, a mailbox, and a number "627" on the wall.

11. 🎰🚶‍♂️ 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 $119
CA $348 total
includes taxes & fees
Nov 2 - Nov 3
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
A room with a closed door, a set of drawers, and a small window.

12. Cozy King Suite

Cozy King Suite
Walkerville
The price is CA $108
CA $217 total
includes taxes & fees
Oct 5 - Oct 6
Cozy King Suite
A living room with a blue sofa, a round wooden coffee table with a plant, a lamp, and a painting on the wall.

13. Walkerville 1BR | WiFi + Workspace + Parking

Walkerville 1BR | WiFi + Workspace + Parking
Walkerville
The price is CA $95
CA $276 total
includes taxes & fees
Oct 26 - Oct 27
Walkerville 1BR | WiFi + Workspace + Parking
A modern living room with a flat-screen TV, a fireplace, a round mirror, and a sofa.

14. Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
The price is CA $125
CA $259 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful gem with amazing view on the riverside
A modern kitchen with white cabinetry, a built-in microwave, and a coffee maker.

15. Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking

Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking
Ford City
9.0 out of 10, Wonderful, (10 reviews)
"Nice stay overall."
United States
Adam Y.
The price is CA $144
CA $306 total
includes taxes & fees
Oct 9 - Oct 10
Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking
A kitchen with a stainless steel refrigerator, a black faucet, a paper towel holder, and a knife block.

16. Stay Together but with Privacy of Two Fully Equipped Apartments

Stay Together but with Privacy of Two Fully Equipped Apartments
Walkerville
The price is CA $136
CA $422 total
includes taxes & fees
Oct 26 - Oct 27
Stay Together but with Privacy of Two Fully Equipped Apartments
A hotel room with a large bed, two windows with curtains, a view of the city, and a small plant.

17. Walkerville 2BR Suite | Near Casino & Free Parking

Walkerville 2BR Suite | Near Casino & Free Parking
Walkerville
10.0 out of 10, Exceptional, (3 reviews)
"Great place for a little weekend stay. Host was friendly and got back to me fast with any answers to my questions. No problems checking in or out. Overall a great stay"
United States
Aidan
The price is CA $157
CA $367 total
includes taxes & fees
Oct 9 - Oct 10
Walkerville 2BR Suite | Near Casino & Free Parking
A residential area with houses, a parking lot, and a large building with a grey roof.

18. Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is CA $99
CA $159 total
includes taxes & fees
Oct 5 - Oct 6
Windsor Perfect Stay
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

19. 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 $245 total
includes taxes & fees
Oct 9 - Oct 10
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
A modern living room with a grey sofa, a white coffee table, and a flat-screen TV on a wooden stand.

20. 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 $121
CA $169 total
includes taxes & fees
Oct 5 - Oct 6
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
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

10/10 Excellent
"Staff was friendly. Room was very nice. Pool and hot tub were always kept up."
Ashton 4-night trip
Posted 1 hour ago
Comfort Inn & Suites Ambassador Bridge

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 top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and live music.

What are some of the best vacation rentals in Windsor?

Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking: 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 111 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 East Riverside Park are a couple of great spots to enjoy the outdoors. You’ll find favorite places to visit like Ford Field and Little Caesars Arena 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.