Compare Vacation Rentals & Airbnb in Windsor

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Windsor vacation rentals
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2034 Rentals and Airbnb in Windsor

Best family friendly Windsor vacation rentals

Among the 2034 accommodations in Windsor, here are the 4 best family friendly rentals

Spacious Corktown Loft Near Downtown, Riverwalk & Michigan Central - 420 Friendly - Windsor
9.3 4 reviews

Spacious Corktown Loft Near Downtown, Riverwalk & Michigan Central - 420 Friendly

apartment, Detroit
This one-bedroom flat is located in Detroit's historic Corktown district, offering easy access to downtown attractions such as the TCF Centre (2.4 kilometres), GM World (2.9 kilometres), Saint Andrew's Hall (3.2 kilometres), Gem Theatre (3.2 kilometres), The Fillmore Detroit (3.2 kilometres), and Music Hall Centre (3.2 kilometres).
This 700 square metre apartment provides accommodation for up to five guests with a separate living room, a fully equipped kitchen featuring an oven and coffee machine, complimentary WiFi, air conditioning, and private parking, with private check-in and check-out also available.
Beautiful Newly Designed Luxurious Apartment - Windsor
8.6 23 reviews

Beautiful Newly Designed Luxurious Apartment

apartment, Windsor
This apartment in Windsor is conveniently located just 3.1 kilometres from the Windsor International Airport, 3.5 kilometres from GM World, and 4 kilometres from the TCF Center, making it ideal for both business travellers and holidaymakers. Guests have consistently rated this property as excellent for its location, cleanliness, and overall experience.
This one-bedroom apartment offers 19 square metres of space and can comfortably accommodate up to four guests. The apartment features a fully-equipped kitchen with a fridge, microwave, dishwasher, and kettle, along with free Wi-Fi, on-site parking, and air conditioning.
Paradise Home - Your Home Away From Home - Windsor
9.2 35 reviews

Paradise Home - Your Home Away From Home

apartment, Windsor
This waterfront property is situated in Windsor, within walking distance of the historic Olde Walkerville neighbourhood and Willistead Manor, making it ideal for exploring the city's rich history and charm. The house has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The house offers a spacious layout, accommodating up to six guests, perfect for families or groups of friends. Guests can enjoy a range of amenities, including a private garden, a jacuzzi, and a fully equipped kitchen, as well as free Wi-Fi and parking.
Stylish 2bd  Dt Laundry And Parking - Windsor
No reviews

Stylish 2bd Dt Laundry And Parking

apartment, Windsor
This Windsor city centre apartment is conveniently located within a 15-minute walk (approximately 1.2km) of the Windsor Community Museum, the Detroit-Windsor Tunnel, and Caesars Windsor.
This 150 square metre self-catering flat sleeps six guests in three bedrooms and two bathrooms, and boasts a private balcony, fitness centre access, and a swimming pool within the building.

Best Windsor vacation rentals with parking

The Hideaway - Windsor
9.9 57 reviews

The Hideaway

apartment, Windsor
This Windsor flat, ideally located in central Windsor, offers easy access to Windsor Castle (distance unspecified), Windsor Great Park (distance unspecified), and Eton (distance unspecified), all within a short distance.
The self-catering apartment sleeps four guests in one bedroom and one bathroom, featuring a kitchen with a fridge and microwave, air conditioning, a garden, parking, and excellent guest reviews; further details on interior design and precise distances to local amenities are needed.
Walk To Riverfront & Caesars Casino  Free Parking - Windsor
9.2 120 reviews

Walk To Riverfront & Caesars Casino Free Parking

apartment, Windsor
This Windsor holiday home on Assumption Street enjoys a prime location, within walking distance of the Detroit-Windsor Tunnel, Caesars Windsor casino, and the Windsor Riverfront.
The three-bedroom, two-bathroom property sleeps six guests and offers a fully equipped kitchen, private garden, free on-site parking (small cars), fast Wi-Fi, and Smart TVs.
Stylish Apt Near Downtown- Ideal For Long Stays! - Windsor
9.1 34 reviews

Stylish Apt Near Downtown- Ideal For Long Stays!

house, Windsor
This newly renovated Windsor apartment, situated in Olde Walkerville, offers easy access to restaurants, the riverfront, and is within 8km of Windsor city centre and its lake views.
The one-bedroom, one-bathroom flat sleeps three guests and boasts a fully equipped kitchen, 55" Smart TV, fast Wi-Fi, and a private two-level layout; nearby attractions include the Casino, Chrysler Theatre, and St. Clair College.
The Parkside Lofts - The Downtown Retreat - Windsor
9.7 6 reviews

The Parkside Lofts - The Downtown Retreat

apartment, Windsor
This 1-bedroom flat is conveniently located for those visiting the University of Windsor, with easy access to waterfront parks, downtown Windsor's amenities, and the U.S. border crossing.
This well-appointed apartment accommodates two guests and features air conditioning, internet, a kitchen with a fridge and microwave, a private bathroom, and a dedicated living and dining area suitable for work or relaxation.

Frequently Asked Questions about vacation rentals in Windsor

  • What should a first-time visitor not miss in Windsor, Ontàrio, Canadà?

    Windsor is a charming city with a rich history and vibrant culture. A first-time visitor should definitely check out the historic Fort Malden, stroll along the beautiful waterfront, and explore the art scene at the Art Gallery of Windsor. You'll also want to take a trip across the Detroit River to the USA and experience the unique atmosphere of Detroit.
  • What are the best Airbnb and vacation rentals in Windsor?

  • Which neighborhood in Windsor, Ontàrio, Canadà should you consider for a vacation rental?

    The Old Walkerville area is a popular choice for a vacation rental, it's got lots of historic buildings and is close to the riverfront. The Sandwich neighbourhood is also a good option, it's a bit quieter but still close to all the action.
  • What are the most popular Airbnbs in Windsor?

  • What are the top family-friendly attractions in Windsor, Ontàrio, Canadà?

    The Windsor International Aquatic Centre is a great place for kids to splash around, and the Ojibway Nature Centre is a great place to learn about the local wildlife. The Windsor Sculpture Park is also a good option, there's plenty of space for kids to run around.
  • What are the best vacation rentals with a pool in Windsor?

  • When is the best time to book a vacation rental in Windsor, Ontàrio, Canadà?

    The best time to book a vacation rental in Windsor is in the spring or autumn, when the weather is mild and there are fewer tourists. If you're looking for a bargain, you can often find good deals in the winter, but be prepared for cold weather.
  • What are the best rentals for families and kids in Windsor?

  • What events or festivals should visitors check out in and around Windsor, Ontàrio, Canadà?

    Windsor hosts a variety of events and festivals throughout the year. The Windsor International Film Festival is a popular event in the fall, while the Windsor Jazz Festival takes place in the summer. The annual Windsor International Wine Festival is another highlight, offering tastings from local and international wineries.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

  • What are the best budget-friendly activities in Windsor, Ontàrio, Canadà?

    The Windsor Sculpture Park is a great free activity, and the Ojibway Nature Centre is also free to enter. If you're looking for a cheap bite to eat, there are plenty of food trucks and cafes in the city.
  • What are the best restaurants with local dishes in Windsor, Ontàrio, Canadà?

    For a taste of local cuisine, try The Colosseum, a popular spot for Italian food, or The Old Mill, which serves up classic Canadian fare. If you're looking for something a bit more casual, The Burger Bar is a great option.
  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a great option for a walk or bike ride, it follows the Detroit River and offers stunning views of the city. The Ojibway Park is also a great place to go for a walk or cycle, there are plenty of trails to explore.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    The Ojibway Nature Centre is a great pet-friendly attraction, there are plenty of trails for dogs to explore. The Windsor Sculpture Park is also pet-friendly, just make sure your dog is on a leash.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy than a hotel room, and they're often more affordable. They can also be a good option for families or groups of friends travelling together.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    The WFCU Centre is home to the Windsor Spitfires hockey team and hosts a variety of other sporting events. The University of Windsor is also home to a number of sporting facilities, including a swimming pool and fitness centre.

Popular destinations

Best Windsor vacation rentals with a balcony

3 Bdr Upper, Prime Location - Windsor
No reviews

3 Bdr Upper, Prime Location

apartment, Windsor
This three-bedroom upper-floor flat in Remington Park, Windsor, offers convenient access to amenities, being a short drive from Devonshire Mall and key cross-border attractions like the Detroit-Windsor Tunnel.
This 111 square metre flat accommodates up to five guests with a fully equipped kitchen, air conditioning, and a terrace or balcony, providing a comfortable base for both work and leisure stays near the Chrysler plant.
Beautifully Renovated Home In Historic Walkerville. - Windsor
10 32 reviews

Beautifully Renovated Home In Historic Walkerville.

apartment, Windsor
This Walkerville apartment is situated 0.5km from Willistead Manor and 2.9km from the Detroit-Windsor Tunnel, offering easy access to the Olde Walkerville neighbourhood and Windsor Riverfront.
This 102 square metre, two-bedroom, two-bathroom flat sleeps four, boasting a fully equipped kitchen, free Wi-Fi, a fireplace, and a terrace; nearby attractions include the Windsor Station (an 18-minute walk away).
Entire Home In Grosse Pointe Park ... Welcome To The Motorcitybnb! - Windsor
10 39 reviews

Entire Home In Grosse Pointe Park ... Welcome To The Motorcitybnb!

apartment, Grosse Pointe Park
This seven-bedroom house is situated in Grosse Pointe Park, a short distance from the centre of Detroit, offering easy access to the Fox Theatre and the Dossin Great Lakes Museum.
This spacious property features a unique automotive theme, including custom car furniture, a working stoplight, a full-size arcade racing game, and seven automotive-themed bedrooms, ideal for large groups of up to 15 guests.
10 Min To Downtown - Fire Pit & Backyard Cinema - Windsor
10 10 reviews

10 Min To Downtown - Fire Pit & Backyard Cinema

apartment, Detroit
This Detroit apartment rental is situated in the North Corktown neighbourhood, a 2.4km walk from both the Detroit Masonic Temple and Michigan Central Station.
The three-bedroom, three-bathroom property sleeps six guests and boasts a fully equipped kitchen, private garden, on-site parking, and air conditioning.

Neighborhoods and points of interest in Windsor

Best Windsor vacation rentals with air conditioning

Cozy South Windsor - Entire Unit, Private Entrance - Windsor
9.5 33 reviews

Cozy South Windsor - Entire Unit, Private Entrance

apartment, Windsor
This Windsor basement flat is conveniently located a 3.2km drive from local supermarkets and within a 16km radius of the Casino Windsor, Ford, Chrysler plants, and the Ambassador Bridge border crossing.
The self-contained unit sleeps two, boasting a queen bed, pull-out sofa, full kitchen with dishwasher, washer/dryer, 4K TV, fireplace, private backyard access with gazebo, and free on-site parking.
The Spacious Nest Exec. Xl Studio Apt. W/parking - Windsor
10 20 reviews

The Spacious Nest Exec. Xl Studio Apt. W/parking

apartment, Windsor
This spacious XXL loft flat is located in a central district of Windsor, offering convenient access to local landmarks.
This pet-friendly accommodation for two guests features a modern, open-plan living space with abundant natural light, a fully equipped kitchen, and an in-suite washer and dryer.
Modern Upscale Sandwich Town Oasis - Windsor
9.8 24 reviews

Modern Upscale Sandwich Town Oasis

house, Windsor
This newly renovated three-bedroom townhome in Windsor's Sandwich Town offers convenient access to both the Ambassador Bridge and the Gordie Howe International Bridge, placing you within easy reach of border crossings.
Sleeping up to six guests, the property boasts two bathrooms, a fully equipped kitchen including a dishwasher, and a peaceful patio; stairs are present.
Walkerville | 3br | 2 Private Apartments - Windsor
10 1 review

Walkerville | 3br | 2 Private Apartments

apartment, Windsor
This Walkerville flat in Windsor is ideally situated for exploring nearby eateries, with downtown Windsor and Caesars Windsor just a short distance away.
This accommodation offers fast Wi-Fi, Smart TVs, dedicated workspaces, and convenient self check-in, alongside free street parking and a unique setup of two private apartments providing both togetherness and privacy for up to six guests.
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