Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

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
10.0 out of 10, Exceptional, (1 review)
"Everything was as describe in profile we made some amazing memories in this house and will return when we come back to visit!"
United States
Carla
The price is CA $193
CA $326 total
includes taxes & fees
Jun 10 - Jun 11
Luxury New Build 4BR Home | Modern Comfort & Style
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, (1 review)
"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 $156
CA $231 total
includes taxes & fees
Jun 8 - Jun 9
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
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 $93
CA $430 total
includes taxes & fees
Jun 18 - Jun 19
Windsor Manor
Interior

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
Jun 11 - Jun 12
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Fridge, microwave, oven, stovetop

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, (17 reviews)
"Great stay! "
Canada
Jade S.
The price is CA $139
CA $251 total
includes taxes & fees
Jun 8 - Jun 9
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South 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
Jun 8 - Jun 9
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Shower, hair dryer, towels, soap

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 $139
CA $189 total
includes taxes & fees
Jun 8 - Jun 9
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Private kitchen

3 Bedroom Upper Unit in the Heart of Windsor

3 Bedroom Upper Unit in the Heart of Windsor
Remington Park
The price is CA $141
CA $306 total
includes taxes & fees
Jul 6 - Jul 7
3 Bedroom Upper Unit in the Heart of Windsor
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
Jun 8 - Jun 9
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
Living area

Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
The price is CA $113
CA $244 total
includes taxes & fees
Jun 8 - Jun 9
Beautiful gem with amazing view on the riverside
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
Jun 8 - Jun 9
Cozy comfort lower level unit
Interior

Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is CA $99
CA $158 total
includes taxes & fees
Jun 8 - Jun 9
Windsor Perfect Stay
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 $56
CA $250 total
includes taxes & fees
Jun 8 - Jun 9
Quaint Clean 2BR DT Windsor Laundry and parking Inc
Interior

Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is CA $82
CA $281 total
includes taxes & fees
Jun 8 - Jun 9
Stylish 2bd DT Laundry and Parking
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
Jun 15 - Jun 16
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
Spa

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 $104
CA $326 total
includes taxes & fees
Jun 9 - Jun 10
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
Interior

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

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
The price is CA $72
CA $146 total
includes taxes & fees
Jun 12 - Jun 13
Affordable 1BHK close to Riverside, Casino, University & USA Border.
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, (20 reviews)
"It was great, short walk to the casino, beds were comfortable and clean."
United States
Luke M.
The price is CA $99
CA $323 total
includes taxes & fees
Jul 6 - Jul 7
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
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, (7 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
Jun 8 - Jun 9
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
Living area

The Best Stay

The Best Stay
Sandwich
2.0 out of 10, (1 review)
"This is not a real place. You follow instructions and they will tell you to leave and it’s not a Vrbo "
United States
Noah G.
The price is CA $98
CA $148 total
includes taxes & fees
Jun 10 - Jun 11
The Best Stay
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

Super 8 by Wyndham Windsor/Dougall

Super 8 by Wyndham Windsor/Dougall

10/10 Excellent
"Clean room"
lokesh 1-night trip
Posted less than an hour ago
Super 8 by Wyndham Windsor/Dougall

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 can relax into your vacation with a garden and a 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 vacation rentals will I find in Windsor?

With 97 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 Lakeshore Woods Walking Trails Trailhead are a couple of great spots to enjoy the outdoors. You’ll find favorite places to visit like Comerica Park 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.