Windsor is a city with both a geographical quirk - it's almost the only place on the border where you go south to enter Canada - and historical infamy. It was once a source for liquor smuggled over the border during prohibition. Today, it offers visitors plenty to see and do while its rich diversity promotes a vibrant gastronomic scene. For your Windsor stay, select short term rental accommodation that ranges from city apartments and historic houses to rustic rural cottages.
Top 15 Recommended vacation rentals in Windsor
Find your perfect vacation rental in Windsor from just $51 per night!
Vacation rentals and apartments with air conditioning
Best vacation rentals with a balcony
Vacation rentals with a fireplace
Budget-friendly Rentals in Windsor
Find Fantastic yet Inexpensive Rentals
Top-Rated Offers and Accommodations in Windsor
Book Vacation Rentals with the Highest User Rating
Why choose HomeToGo?
Securely pay and stay your way
Choose local, trusted payment methods, plus trip insurance and add-on services.
Award-winning customer service
Experience seamless, hands-on support for any booking questions or concerns.
Verified reviews
Trust in the quality and comfort of your stay with verified guest reviews.
Price clarity, no surprises
Spend your budget exactly as planned by comparing thousands of providers.
Smart search made simple
Transform vacation planning into a joy with advanced, AI-powered search tools.
Find your dream stay
Explore 15 million+ rentals, the world’s biggest selection of vacation homes.
Popular Rental Amenities in Windsor
Windsor is a fantastic vacation destination if you want a property with a pool, as 26% of the vacation rentals there have one. Additionally, more House rental have pools than any other accommodation type. They are a great choice if you go in a group of 4, as that is the number of people they can usually accommodate. You can also find and book a vacation home providing a pool near the water, which is the case for many of the rentals in this destination.
What are the best places to discover the arts and culture of Windsor?
Windsor's Art and Cultural scene
If the sun is shining, visit Windsor Sculpture Park with its 35 huge exhibits.
Alternatively, if the weather isn't so good, spend a couple of hours at the Art Gallery of Windsor.
This long-established venue has one of the country's best displays of Canadian art.
What are the must-see attractions in Windsor?
While Away the Hours in Windsor
Explore Windsor's History
A historic site close to any Windsor accommodation is Willistead Manor, designed in the Tudor-Jacobean style by Albert Kahn. Inside are many rooms to explore while its beautiful grounds play host to Arts in the Park every June. François Bâby House is now home to Windsor's Community Museum while the Sandwich First Baptist Church was established by successful users of the Underground Railroad.
Ojibwe Prairie Complex
Plan a day out from your short term rental with a visit to the Ojibway Prairie Complex. Hike or cycle through its different nature reserves before learning about its history, flora and fauna in the Educational Centre. Keep an eye out for a huge variety of birds as well as lizards, frogs, turtles, snakes and, in the evening, bats.
Roy A. Battagello River Walk Bike Trail
Enjoy a few hours on the eight-kilometre long Roy A. Battagello River Walk Bike Trail. It winds its way from Ambassador Bridge through Downtown Windsor to Dieppe Gardens and the Windsor Sculpture Park. Take time out to enjoy the views or tuck into a picnic prepared in your Windsor accommodation.
Adventure Bay Family Water Park
Close to your Windsor accommodation is Adventure Bay Family Water Park, perfect for family fun. It features five waterslides from the toddler-friendly Tot Loch to the thrilling Python along with a wave pool, lazy river, surf simulator and giant adventure playground.
Sandpoint Beach
Sandpoint Beach will be close to your Windsor accommodation wherever you choose to stay. Spend a lazy day swimming and sunbathing or take to the water for paddle boarding and windsurfing.
Information about vacation rentals in Windsor
| 🏡 Vacation rentals available | 699 rentals |
|---|---|
| 🌙 Nightly prices starting at | $51 |
| ⭐ Popular amenities | Internet, Pets allowed and Pool |
| 🐾 Pet friendly homes | 219 homes |
| 🏊 Vacation rentals with pools | 183 homes |
Frequently Asked Questions
What is the typical availability of vacation rentals in Windsor?
At the moment, there are 699 vacation homes from 8 different providers in Windsor.
What are the most popular vacation home amenities in Windsor?
When looking to book a vacation home in Windsor, the most requested amenities include Internet, Pets allowed, and Pool.
Are there pet-friendly vacation rentals in Windsor?
Yes, there are 219 pet-friendly vacation rentals in Windsor, with an average nightly price of $214.
What's the best month to book a vacation rental in Windsor?
If you're looking for balmy weather, July and August are typically the hottest months in Windsor with temperatures around 27 °C. January and February in Windsor are the coldest, with -8 °C on average.
Top cities to visit
Find more vacation rental types in Windsor
Top Vacation Destinations
- Canada Vacation Rentals
- Toronto Vacation Rentals
- Whistler Vacation Rentals
- Calgary Vacation Rentals
- Prince Edward Island Vacation Rentals
- Edmonton Vacation Rentals
- Canmore Vacation Rentals
- Ottawa Vacation Rentals
- Nova Scotia Vacation Rentals
- Kelowna Vacation Rentals
- Mont-Tremblant Vacation Rentals
- Algonquin Park Vacation Rentals
- Sauble Beach Vacation Rentals
- Ucluelet Vacation Rentals
- Vancouver Island Vacation Rentals
- Grand Bend Vacation Rentals
- Alberta Vacation Rentals
- Cavendish Vacation Rentals
- Niagara Falls NY Vacation Rentals
- Niagara-on-the-Lake Vacation Rentals
- British Columbia Vacation Rentals
- Revelstoke Vacation Rentals
- Sun Peaks Vacation Rentals
- Manitoba Vacation Rentals
- New York Vacation Rentals
- Cape Breton Island Vacation Rentals
- Cape Breton Island Vacation Rentals
- Mississauga Vacation Rentals
- Fernie Vacation Rentals
- Maui Vacation Rentals
- Wasaga Beach Vacation Rentals
- Osoyoos Vacation Rentals
- London Vacation Rentals
- Paris Vacation Rentals
- Hamilton Vacation Rentals
- Saskatoon Vacation Rentals
- Long Beach Vacation Rentals
- Barrie Vacation Rentals
- Port Renfrew Vacation Rentals
- Costa Rica Vacation Rentals
- Saskatchewan Vacation Rentals
- Palm Springs Vacation Rentals
- Winnipeg Vacation Rentals
- Brampton Vacation Rentals
- Orlando Vacation Rentals
- Waskesiu Lake Vacation Rentals
- Squamish Vacation Rentals
- Parksville Vacation Rentals
- Collingwood Vacation Rentals
- Harrison Hot Springs Vacation Rentals
- Kamloops Vacation Rentals
- Waterton Vacation Rentals
- Ingonish Vacation Rentals
- Miami Vacation Rentals
- Lake Louise Vacation Rentals
- Oakville Vacation Rentals
- Penticton Vacation Rentals
- Sooke Vacation Rentals
- Bowen Island Vacation Rentals
- Radium Hot Springs Vacation Rentals