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Windsor Vacation Rentals

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Vacation Rentals in Windsor

Drifted Inn - Riverfront Cottage

Drifted Inn - Riverfront Cottage

942 Front Rd S, Amherstburg, ON

Nestled on the beach, this Amherstburg cottage is 2.3 mi (3.6 km) from Fort Malden National Historic Site and 2.3 mi (3.7 km) from Lake Erie. Essex County ATV ...

4.9/5Exceptional! (61 reviews)

"This is a great little getaway and close to wineries and golf courses to explore. When just relaxing, the view is great especially fun to watch the large boats go by."…"

Reviewed on Oct. 18, 2020

Drifted Inn - Riverfront Cottage
Waterfront Cottage in a 200 Acre Conservation Area

Waterfront Cottage in a 200 Acre Conservation Area

6952 County Road 50 West, N0R 1G0, Amherstburg, ON

Situated in Amherstburg, this beach cottage is 2.2 mi (3.6 km) from Lake Erie and within 20 miles (32 km) of St. Clair College and Devonshire Mall. Detroit Windsor ...

4.9/5Exceptional! (15 reviews)
Just what we needed

"This cottage is a hidden gem. Contains everything you could possibly need-gorgeous views from every window. You’d think you were far north! Great walking trails, peaceful and clean. Loved our stay & already thinking of booking again."…"

Reviewed on Oct. 20, 2020

Waterfront Cottage in a 200 Acre Conservation Area
Bootleggers Bunker in Historic Walkerville 2bd/1ba

Bootleggers Bunker in Historic Walkerville 2bd/1ba

1207 Monmouth Rd, 4, Windsor, ON
The price is CA $139 per night from Nov 11 to Nov 12

Located in Walkerville, this apartment building is 0.7 mi (1.2 km) from Walkerville Brewery and within 3 miles (5 km) of Detroit Windsor Tunnel and Caesars Casino. ...

Bootleggers Bunker in Historic Walkerville 2bd/1ba

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Hall House: Entire House for Your Stay

Hall House: Entire House for Your Stay

876 Hall Ave, Windsor, ON

Located in Walkerville, this holiday home is within 1 mi (2 km) of Walkerville Brewery and Detroit Windsor Tunnel. Caesars Casino and University of Windsor are ...

5/5Exceptional! (1 review)

"The area was quiet, and the house was beautiful. Would definitely recommend a stay"…"

Reviewed on Aug. 3, 2020

Hall House: Entire House for Your Stay
Willowood RV Resort

Willowood RV Resort

2 out of 5
4610 Essex County Rd 18, RR1, Amherstburg, ON

Situated in Amherstburg, this cabin is within 9 miles (15 km) of Fort Malden National Historic Site, Essex County ATV Club Trails Trailhead - West and Lake Erie. ...

Willowood RV Resort
NEW Luxury, Willow Beach Cottage Steps to the Lake

NEW Luxury, Willow Beach Cottage Steps to the Lake

94 Willow Beach Rd, Amherstburg, ON

Situated near the beach, this holiday home is 0.1 mi (0.1 km) from Lake Erie and within 25 miles (40 km) of Detroit Windsor Tunnel and Caesars Casino. University ...

5/5Exceptional! (10 reviews)
Relaxing getaway close to home

"This was an absolutely fabulous property. It exceeded our expectations! If this property was available as a permanent rental, I would jump on the chance to rent it for my husband and I (retired). It's the perfect little home."…"

Reviewed on Oct. 23, 2020

NEW Luxury, Willow Beach Cottage Steps to the Lake
Beautiful Renovated Ground Floor Unit - Downtown Windsor

Beautiful Renovated Ground Floor Unit - Downtown Windsor

641 Dougall Ave, Windsor, ON

Situated in Windsor, this apartment building is within 1 mi (2 km) of Adventure Bay Family Water Park, Detroit Windsor Tunnel, and Caesars Casino. University ...

5/5Exceptional! (1 review)
Very clean, central, good amount of space

"Clean and central to many places - I was able to walk to the library and museums for research. The riverside trail is just a ten minute walk and it's lovely. There is a Food Basics a ten minute walk southeast. They have a washer and dryer downstairs. The street parking was mostly no trouble; I only ..."…"

Reviewed on Sep. 15, 2019

Beautiful Renovated Ground Floor Unit - Downtown Windsor
Residence & Conference Centre - Windsor

Residence & Conference Centre - Windsor

2 out of 5
3995 Geraedts Drive, Windsor, ON

Situated near the airport, this residence is 0.3 mi (0.6 km) from St. Clair College and 2.9 mi (4.6 km) from Devonshire Mall. Adventure Bay Family Water Park ...

4/5Very Good! (293 reviews)

"Typical residence with all that one would (and wouldn't) expect in terms of amenities and organization."…"

Reviewed on Aug. 24, 2019

Residence & Conference Centre - Windsor
Beautifully Renovated Home in Historic Walkerville

Beautifully Renovated Home in Historic Walkerville

1109 Chilver Rd, Windsor, ON

Located in Walkerville, this historic apartment building is within 2 mi (3 km) of Walkerville Brewery, Detroit Windsor Tunnel, and Caesars Casino. Chrysler Theatre ...

5/5Exceptional! (8 reviews)
Amazjng home, fantastic location

"We absolutely loved this place! It was very clean and comfortable and we enjoyed the many amenities offered through the house. The location was perfect for walking to many restaurants, shops and learning about the many historical homes in the walkerville area. We would definitely stay here ..."…"

Reviewed on Feb. 14, 2020

Beautifully Renovated Home in Historic Walkerville
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See all available properties in Windsor
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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.

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.

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’s there to see and do in Windsor?
Cultural attractions include Leamington Arts Centre and Chrysler Theatre, whereas Point Pelee National Park and Lake Erie are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Detroit Windsor Tunnel and Caesars Casino.
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.

Other types of properties in Windsor you may be interested in

Travelodge by Wyndham Windsor

Travelodge by Wyndham Windsor

2 out of 5
2225 Division Rd, Windsor, ON
Free cancellationReserve now, pay when you stay
The price is CA $64 per night from Nov 13 to Nov 14
Travelodge by Wyndham Windsor
Lexington Inn & Suites Windsor

Lexington Inn & Suites Windsor

2.5 out of 5
2130 Division Road, Windsor, ON
Free cancellationReserve now, pay when you stay
The price is CA $72 per night from Oct 28 to Oct 29
Lexington Inn & Suites Windsor
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.