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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Windsor vacation rentals

Smart TV, fireplace

Luxury New Build 4BR Home | Modern Comfort & Style

Luxury New Build 4BR Home | Modern Comfort & Style
Ford City
9.4 out of 10, Exceptional, (3 reviews)
"Nice stay overall."
United States
Adam Y.
The price is CA $181
CA $308 total
includes taxes & fees
Jul 20 - Jul 21
Luxury New Build 4BR Home | Modern Comfort & Style
Lobby sitting area

Residence & Conference Centre - Windsor

Residence & Conference Centre - Windsor
2.0 star property
Roseland
8.2 out of 10, Very good, (445 reviews)
"A great place and great value,especially for the family with kids, clean and nice staff."
Canada
BIN
The price is CA $82
CA $92 total
includes taxes & fees
Jul 13 - Jul 14
Residence & Conference Centre - Windsor
Fridge, microwave, oven, stovetop

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 CA $171
CA $259 total
includes taxes & fees
Jul 13 - Jul 14
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Interior

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
Jul 13 - Jul 14
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
1 bedroom, desk, iron/ironing board, free WiFi

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, (3 reviews)
"Was the perfect space to stay when we went to a concert at the Casino. Uber about 15 each way. So much cheaper than a hotel & so nice. Clean, new & a great host! "
Canada
Kirby B.
The price is CA $115
CA $169 total
includes taxes & fees
Jul 26 - Jul 27
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
Smart TV, fireplace, books

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, (8 reviews)
"Such a cool place with loads of room but also very charming by design "
Canada
melinda
The price is CA $275
CA $468 total
includes taxes & fees
Jul 13 - Jul 14
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
Fridge, microwave, oven, stovetop

Modern Spacious 1 bedroom and a den home (Lower Unit)

Modern Spacious 1 bedroom and a den home (Lower Unit)
Roseland
8.6 out of 10, Excellent, (7 reviews)
"was a great property and location"
United States
Ava C.
The price is CA $225
CA $485 total
includes taxes & fees
Jul 13 - Jul 14
Modern Spacious 1 bedroom and a den home (Lower Unit)
Smart TV

Cozy comfort lower level unit

Cozy comfort lower level unit
Roseland
9.0 out of 10, Wonderful, (12 reviews)
"We enjoyed our stay very much."
Canada
Amanda
The price is CA $100
CA $190 total
includes taxes & fees
Jul 13 - Jul 14
Cozy comfort lower level unit
Interior

Quaint Clean 2BR DT Windsor Laundry and parking Inc

Quaint Clean 2BR DT Windsor Laundry and parking Inc
City Centre
2.0 out of 10, (1 review)
"We must state that this place was very clean, the sheets and towels smelled nice, and the beds were comfortable; however, it is a very old basement where only a furnace and root cellar should be located. The floor is all uneven and multi levels, it is very poorly finished, we had zero control of the heat, and there are no useable windows. The table is very rickety. The site photos are deceiving; we were not impressed, and it was very over-priced for the lack of quality."
United States
Sandra H.
The price is CA $74
CA $275 total
includes taxes & fees
Jul 13 - Jul 14
Quaint Clean 2BR DT Windsor Laundry and parking Inc
TV

Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Walkerville
10.0 out of 10, Exceptional, (1 review)
"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
Jul 13 - Jul 14
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Smart TV

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 $135
CA $252 total
includes taxes & fees
Jul 13 - Jul 14
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
Iron/ironing board, WiFi

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

3 Bedrooms, 2 Kitchens & 2 Bathrooms—Perfect for Groups
Walkerville
The price is CA $148
CA $448 total
includes taxes & fees
Jul 15 - Jul 16
3 Bedrooms, 2 Kitchens & 2 Bathrooms—Perfect for Groups
Smart TV

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 $92
CA $432 total
includes taxes & fees
Jul 16 - Jul 17
Windsor Manor
Interior

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

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
The price is CA $76
CA $150 total
includes taxes & fees
Aug 3 - Aug 4
Affordable 1BHK close to Riverside, Casino, University & USA Border.
Fridge, microwave, oven, stovetop

Walkerville 1BR Apartment | WiFi + Workspace

Walkerville 1BR Apartment | WiFi + Workspace
Walkerville
The price is CA $61
CA $214 total
includes taxes & fees
Jul 13 - Jul 14
Walkerville 1BR Apartment | WiFi + Workspace
Interior

Penthouse suite in heart of little Italy

Penthouse suite in heart of little Italy
Walkerville
8.8 out of 10, Excellent, (15 reviews)
"Amazing place, Incredible host, very easy to talk to. Will comeback again for sure!! "
United States
Benz V.
The price is CA $270
CA $444 total
includes taxes & fees
Jul 13 - Jul 14
Penthouse suite in heart of little Italy
Exterior detail

🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9

🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Walkerville
9.2 out of 10, Wonderful, (19 reviews)
"It was great, very short walk to the casino!"
United States
tiara t.
The price is CA $130
CA $363 total
includes taxes & fees
Aug 12 - Aug 13
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Interior

Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is CA $105
CA $166 total
includes taxes & fees
Jul 13 - Jul 14
Windsor Perfect Stay
Interior

Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is CA $83
CA $284 total
includes taxes & fees
Jul 13 - Jul 14
Stylish 2bd DT Laundry and Parking
Living area

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
Jul 19 - Jul 20
Beautiful gem with amazing view on the riverside
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

Hyatt Place Windsor

Hyatt Place Windsor

10/10 Excellent
"good breakfast"
Vincent C. S. 2-night trip
Posted 9 hours ago
Hyatt Place Windsor

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?

🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9: Visitors give good reviews to this Windsor vacation home rental, which is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind. Some other homes for rent in Windsor include Luxury getaway with pool and hot tub - family retreat and Waterfront Retreat: 6BR Home, BBQ, Sleeps 10.

How many vacation rentals will I find in Windsor?

With 104 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 Dieppe Gardens, 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 Caesars Casino and Ford Field 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.