Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

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
The price is CA $162
CA $286 total
includes taxes & fees
May 25 - May 26
Luxury New Build 4BR Home | Modern Comfort & Style
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
May 27 - May 28
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
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
8.8 out of 10, Excellent, (10 reviews)
"This stay exceeded our expectations. Would definitely recommend."
Canada
Natalie
The price is CA $171
CA $259 total
includes taxes & fees
May 19 - May 20
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
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
May 17 - May 18
Beautiful gem with amazing view on the riverside
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
May 17 - May 18
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
Interior

Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is CA $99
CA $158 total
includes taxes & fees
May 18 - May 19
Windsor Perfect Stay
2 bedrooms, desk, iron/ironing board, travel crib

Cheerful Family Home 3 mins drive to UWindsor

Cheerful Family Home 3 mins drive to UWindsor
Bridgeview
The price is CA $118
CA $388 total
includes taxes & fees
Jun 8 - Jun 9
Cheerful Family Home 3 mins drive to UWindsor
Outdoor dining

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
May 20 - May 21
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
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
8.4 out of 10, Very good, (6 reviews)
"was a great property and location"
United States
Ava C.
The price is CA $225
CA $483 total
includes taxes & fees
May 17 - May 18
Modern Spacious 1 bedroom and a den home (Lower Unit)
Interior

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
May 27 - May 28
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
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)
"Nice, clean place close to the riverside."
United States
Dawn P.
The price is CA $146
CA $265 total
includes taxes & fees
May 18 - May 19
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
TV

Clean and spacious 3BR DT Windsor Laundry and parking

Clean and spacious 3BR DT Windsor Laundry and parking
City Centre
The price is CA $93
CA $356 total
includes taxes & fees
May 18 - May 19
Clean and spacious 3BR DT Windsor Laundry and parking
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 $79
CA $411 total
includes taxes & fees
May 31 - Jun 1
Windsor Manor
Interior

Penthouse suite in heart of little Italy

Penthouse suite in heart of little Italy
Walkerville
8.8 out of 10, Excellent, (15 reviews)
"Beautiful, clean"
United States
Kimberly A.
The price is CA $270
CA $444 total
includes taxes & fees
May 17 - May 18
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
9.0 out of 10, Wonderful, (17 reviews)
"It was great, short walk to the casino, beds were comfortable and clean."
United States
Luke M.
The price is CA $76
CA $295 total
includes taxes & fees
May 18 - May 19
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Smart TV

Cozy comfort lower level unit

Cozy comfort lower level unit
Roseland
9.6 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay very much."
Canada
Amanda
The price is CA $75
CA $162 total
includes taxes & fees
May 18 - May 19
Cozy comfort lower level unit
Living area

Black Door Bungalow, a stylishly renovated

Black Door Bungalow, a stylishly renovated
Walkerville
The price is CA $117
CA $220 total
includes taxes & fees
May 17 - May 18
Black Door Bungalow, a stylishly renovated
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
May 23 - May 24
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
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
May 18 - May 19
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Comfort Inn Windsor

Comfort Inn Windsor

8/10 Good
"Tout était très bien. Personnel courtois 😊"
Lovely 2-night trip
Posted 6 hours ago
Comfort Inn 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 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?

🎰🚶‍♂️ 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 Cozy comfort lower level unit and Luxury getaway with pool and hot tub - family retreat .

How many vacation rentals will I find in Windsor?

With 98 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 Coventry Gardens 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.