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 $74 per night!
Vacation rentals and apartments with air conditioning
Best vacation rentals with a balcony
Vacation rentals with a fireplace
Best Vacation Home Deals in Windsor
Save up to 17%
631 fantastic vacation rentals from 9 vacation rental websites are available in Windsor, with prices beginning at $74 per night. Using HomeToGo's search feature you can instantaneously search and compare the offers of each listed rental to discover the best deal and save up to 17%.
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 27% 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 9, 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.
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.
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 | 631 rentals |
---|---|
💳 Possible discounts | up to 17% |
🌙 Nightly prices starting at | $74 |
⭐ Popular amenities | Internet, Pets allowed and Pool |
🐾 Pet friendly homes | 154 homes |
🏊 Vacation rentals with pools | 173 homes |
Frequently Asked Questions
What is the typical availability of vacation rentals in Windsor?
At the moment, there are 631 vacation homes from 9 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 154 pet-friendly vacation rentals in Windsor, with an average nightly price of $248.
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 Vacation Destinations
- Vacation Rentals in Canada: A Gateway to Vast Adventures and Fun
- Jasper Vacation Rentals Open Up a World of Adventure Amid Nature
- Book the perfect getaway with a Tofino vacation rental
- Explore Toronto From Your a Modern Vacation Apartment Rental
- Banff Vacation Rentals: Scenic Views & Unparalleled Natural Beauty For Your Perfect Vacation
- Kick Back and Sail Down the Slopes from a Whistler Vacation Rental
- Beaches, seafood and history from PEI Vacation Rentals
- Spend your summer vacation at a waterfront cottage in Tobermory, Ontario
- Discover a West Coast culture hub with a condo rental in Vancouver
- Enjoy Canada's culture and waterfront scenery from an Ontario cottage rental
- Have a great holiday at an Ottawa vacation rental
- Discover the best of Kelowna with a vacation home rental
- Escape to the mountains from a Canmore cabin rental
- Have a Fantastic Stay in a Calgary Vacation Rental
- Have a Fantastic Vacation with a Montreal Rental Apartment
- Enjoy a stay near Algonquin Park in a cosy rental cabin
- Take a coastal break in a Nova Scotia vacation rental
- Have a Fun Retreat at Cultus Lake Cabin Rentals
- Experience Edmonton with a great vacation rental
- Whale Watching, Fresh Oysters, and Cozy Cabin Rentals in Ucluelet
- Relax with a vacation home in beautiful Osoyoos
- Discover fun for the whole family with a Wasaga Beach cottage rental
- Access History and Culture With a Cabin in Victoria
- History and Exciting Outdoors with a Cozy Vacation Home in Mississauga
- Vacation Rentals in Revelstoke to Experience the Outdoors
- Nature and Waters with Idyllic Vacation Rental in Lake Louise
- Have a fantastic Vacation in a Halifax Cottage
- Relax at Port Renfrew Vacation Homes: Vancouver Island's Best
- Enjoy year-round adventures at Sun Peaks cabin rentals
- Discover the South Bruce Peninsula From a Sauble Beach Vacation Home
- Holiday in comfort and style at Vancouver Island cabin rentals
- Get cozy in your very own Cape Breton Island vacation rental
- Find Your Ideal Vacation Rental on Beautiful Cape Breton Island
- Mont-Tremblant awaits with your vacation rental
- White Sandy Beaches and Organic Local Produce on Hornby Island
- Enjoy a Beachside Break at a Parksville Vacation Rental
- Discover Your Ideal Vacation Home in Lakeside Harrison Hot Springs
- Treat your family to a vacation rental on Bowen Island
- Beaches and Local Delights with a Charming Ingonish Vacation Rental
- Enjoy breathtaking nature with a Niagara Falls vacation home
- A vacation home in the "Chicago of the North," Winnipeg
- Find Your Ideal Vacation Rental in Beautiful Fernie, BC
- Get Back to Nature in an Alberta Vacation Rental
- Enjoy the Unforgettable Sunshine Coast with a Local Vacation Rental
- Fun in Collingwood with a Beautiful Cottage Rental
- From pristine slopes to foodie festivals with Barrie vacation rentals
- Experience a Dream Canadian Getaway with a Kamloops Vacation Home
- Enjoy High Altitude Adventures With Mount Washington Vacation Rentals
- Experience Québec's vibrant heritage from your vacation rental
- Explore Unique Outdoor Activities with a Saskatoon Vacation Rental