Vacation Rentals in Windsor

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Windsor holiday rentals
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1448 Holiday rentals and Airbnb in Windsor

Best family friendly Windsor holiday rentals

Among the 1448 accommodations in Windsor, here are the 4 best family friendly rentals

Clean 4 Br Home With Karaoke And Arcades - Windsor
9.9 51 reviews
Windsor
25/06 – 27/06
A$347/nighttotal: A$694 (2 )

Clean 4 Br Home With Karaoke And Arcades

1 3
apartment , Windsor
This detached bungalow in Windsor offers a family-friendly stay with excellent ratings for location, cleanliness, and user experience.
This four-bedroom property accommodates up to eight guests and includes a full kitchen, laundry facilities, Wi-Fi, air conditioning, and parking, with entertainment provided by a karaoke system and arcade machines.
Large Quiet Estate Property In Beautiful Natural Surroundings. - Windsor
9.8 126 reviews
Windsor
16/11 – 07/12
A$660/nighttotal: A$13860 (21 )

Large Quiet Estate Property In Beautiful Natural Surroundings.

6 4
apartment , Windsor
This luxurious home is situated on Windsor's finest golf course, just minutes from the Ambassador Bridge connecting to Detroit, Michigan, offering scenic views and a peaceful atmosphere. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious six-bedroom property is beautifully furnished and designed, providing ample space for large groups or families. The home offers a private pool, hot tub, yoga room, outdoor kitchen and bar, and full access to the estate, creating a resort-like experience.
Olde Walkerville Wonder! - Windsor
Windsor
13/07 – 17/08
A$104/nighttotal: A$3640 (35 )

Olde Walkerville Wonder!

1 2
apartment , Windsor
This Olde Walkerville flat is situated in Windsor's historic district, offering immediate access to restaurants, breweries, cafes, and the Detroit River waterfront trail, approximately 200 metres away.
This one-bedroom, one-bathroom apartment accommodates up to three guests and includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, and a private garden, with keypad entry for secure access.
Comfort Home - Windsor
9.7 76 reviews
Windsor
27/06 – 04/07
A$192/nighttotal: A$1344 (7 )

Comfort Home

1 1
apartment , Windsor
This modern four-bedroom house, sleeping up to eight guests, is situated in Windsor, within a 5km radius of Windsor town centre, the River Thames, and the historic Royal Windsor Castle.
The property features two ground-floor and two upstairs bedrooms, two bathrooms, a fully equipped kitchen (fridge, freezer, microwave), air conditioning, parking, and excellent Wi-Fi; it's perfect for families or groups visiting Windsor's attractions.

Best Windsor holiday rentals with parking

Navy Gold Dream - 2 Bedroom House W/ Work Station - Windsor
9.8 75 reviews
Windsor
01/09 – 18/12
A$99/nighttotal: A$10692 (108 )

Navy Gold Dream - 2 Bedroom House W/ Work Station

2 1
apartment , Windsor
This semi-detached house is located in a residential area, just 3 kilometres from Ottawa Street and 9 kilometres from Windsor city centre. The property has received excellent ratings for location, cleanliness and overall user experience.
The house has two bedrooms and can accommodate up to four guests. Guests can enjoy a comfortable stay with amenities such as a fully equipped kitchen, air conditioning, a garden, free parking, and high-speed Wi-Fi.
Motorcity Haven In The Heart Of Downtown Detroit - Windsor
9.0 23 reviews
Windsor
30/06 – 02/07
A$577/nighttotal: A$1154 (2 )

Motorcity Haven In The Heart Of Downtown Detroit

3 6
apartment , Detroit
This North Corktown flat is ideally situated in Downtown Detroit, within walking distance of Little Caesars Arena, Ford Field, Comerica Park, and the MotorCity Casino.
The 158-square-metre (1700 sq ft) three-bedroom, two-bathroom dwelling sleeps twelve guests and offers amenities including a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, smart home technology, and free Wi-Fi.
Studio Apartment | Close To Windsor-detroit Tunnel - Windsor
Windsor
13/07 – 17/08
A$152/nighttotal: A$5320 (35 )

Studio Apartment | Close To Windsor-detroit Tunnel

1 2
studio , Windsor
This Walkerville studio apartment in Windsor enjoys a central location near the Detroit-Windsor Tunnel and Ambassador Bridge, providing easy access to Detroit's Comerica Park and Ford Field.
The self-contained unit offers a one-bedroom, one-bathroom layout sleeping up to two guests, and includes a fridge, microwave, dishwasher, air conditioning, parking, and internet access.
Open Loft W/water Bridge View 2mins To Dwntn - Windsor
8.8 38 reviews
Windsor
27/06 – 28/06
A$383/nightfor 1 night

Open Loft W/water Bridge View 2mins To Dwntn

1 2
apartment , Detroit
This Detroit apartment offers a convenient city-centre location, less than 1.6km from the Detroit Riverwalk and within 3.2km of major attractions such as Huntington Place, the MGM Grand Detroit Casino, and Little Caesars Arena.
The one-bedroom flat sleeps two guests and includes a fully equipped kitchen with oven, hob, microwave, and fridge, in-unit laundry, free Wi-Fi, and a Smart TV; nearby attractions include the Joe Louis Arena and Fort Cass train stations.

Frequently asked questions about holiday rentals in Windsor

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

    The Windsor Sculpture Park is a great place for a family stroll, with its collection of outdoor sculptures. For a fun day out, visit the Hands-On Museum, with interactive exhibits for kids of all ages. Also, the Ojibway Nature Centre is a popular spot for families to enjoy nature trails and wildlife viewing.
  • What are the best Airbnb and holiday rentals 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 during the shoulder seasons, spring and autumn, when the weather is mild and there are fewer crowds. For a more affordable option, consider booking during the winter months, but be prepared for colder temperatures.
  • What are the most popular Airbnbs in Windsor?

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

    Take a walk or bike ride along the scenic Windsor Riverfront Trail, which stretches for 14 kilometres along the Detroit River. You can also visit the free exhibits at the Windsor Public Library or the Mackenzie Hall, a historic landmark.
  • What are the best holiday rentals with a pool in Windsor?

  • What are the best restaurants with local dishes in Windsor, Ontàrio, Canadà?

    For a taste of Windsor's culinary scene, try The Twisted Apron, known for its fresh, locally sourced ingredients. Another popular spot is The Colosseum, serving up classic Italian dishes. And for a casual dining experience, The Old Stone Mill Pub offers traditional pub fare.
  • What are the best rentals for families and kids in Windsor?

  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Windsor Riverfront Trail is a great option for a leisurely walk or bike ride, offering stunning views of the Detroit River. For a more challenging ride, try the Ojibway Park trails, which wind through the park's natural woodlands and wetlands.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    Yes, many parks and green spaces in Windsor are pet-friendly, including the beautiful Ojibway Park, where you can enjoy a walk with your furry friend. The Windsor Riverfront Trail is also a great option for a stroll with your dog.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy compared to hotels, and often come with amenities such as a kitchen, making it easier to prepare meals. They can also be a more affordable option, especially for families or groups travelling together.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    The WFCU Centre is home to the Windsor Spitfires, a junior ice hockey team, and hosts various sporting events throughout the year. The University of Windsor is also home to a variety of sports facilities, including a swimming pool, a gym, and a track and field stadium.

Destinations nearby

Best Windsor holiday rentals with a balcony

Windsor Luxury Oasis - Windsor
10 3 reviews
Windsor
15/12 – 28/12
A$845/nighttotal: A$10985 (13 )

Windsor Luxury Oasis

4 4
house , Windsor
This South Windsor property offers a tranquil retreat, situated conveniently 12.56 kilometres from the TCF Centre, 11.91 kilometres from GM World, and a mere 4 kilometres from Windsor International Airport.
This spacious 279 square metre holiday home accommodates up to 14 guests across its 3 bathrooms and 1 bedroom, featuring a saltwater swimming pool, a garden, air conditioning, and a fully equipped kitchen with a dishwasher and oven, all complemented by complimentary WiFi.
7br House 19 Ppl Dt Windsor Wd Free Parking - Windsor
Windsor
03/10 – 07/10
A$978/nighttotal: A$3912 (4 )

7br House 19 Ppl Dt Windsor Wd Free Parking

1 2
house , Windsor
Holiday house rental. You will be in Windsor.
Services and facilities: a washing machine, an iron and a kitchen. This house in Windsor also has a terrace!
Loft W Fenced Yard Pet-friendly Near Downtown - Windsor
Windsor
03/10 – 07/10
A$280/nighttotal: A$1120 (4 )

Loft W Fenced Yard Pet-friendly Near Downtown

1 2
apartment , Detroit
This pet-friendly loft in Detroit offers a fenced yard and is situated approximately 4.8 to 6.4 kilometres from downtown attractions including the TCF Centre, Gem Theatre, and Detroit Symphony Orchestra Hall.
This 51 square metre apartment accommodates up to seven guests, featuring a balcony, communal garden, full kitchen with microwave, free WiFi, and private parking.
Beautifully Renovated Home In Historic Walkerville. - Windsor
10 30 reviews
Windsor
27/06 – 04/07
A$223/nighttotal: A$1561 (7 )

Beautifully Renovated Home In Historic Walkerville.

2 2
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).

Best Windsor holiday rentals with air conditioning

Stylish 2-bedroom Apartment In Downtown Windsor - Windsor
8.8 32 reviews
Windsor
15/12 – 28/12
A$167/nighttotal: A$2171 (13 )

Stylish 2-bedroom Apartment In Downtown Windsor

2 4
apartment , Windsor
This stylish Windsor city centre flat is situated within 3.2km of the TCF Centre, 2.4km from the GM World, and under 3.2km from several theatres.
The 84 square metre property features two bedrooms, one bathroom, sleeps seven guests, and includes free Wi-Fi, a fully equipped kitchen, air conditioning, parking, and a washer.
Modern Walkerville Unit - Steps From Riverfront! - Windsor
10 13 reviews
Windsor
13/07 – 17/08
A$82/nighttotal: A$2870 (35 )

Modern Walkerville Unit - Steps From Riverfront!

2 2
apartment , Windsor
This newly renovated two-bedroom apartment in Windsor's Walkerville neighbourhood is a short distance from Willistead Manor.
The self-contained flat offers a spacious open-plan living/dining area, a fully equipped kitchen, private laundry, and a shared patio and BBQ, sleeping up to three guests.
Cozy 2-bedroom Suite Near Walkerville - Windsor
8.8 16 reviews
Windsor
28/06 – 31/07
A$87/nighttotal: A$2871 (33 )

Cozy 2-bedroom Suite Near Walkerville

1 2
apartment , Windsor
This Windsor apartment, located in the Walkerville neighbourhood, is minutes from the Detroit-Windsor Tunnel and Bridge, offering easy access to Detroit's sporting venues.
The two-bedroom, one-bathroom flat sleeps four guests and features a spacious kitchen with fridge, freezer, and microwave, plus complimentary toiletries, internet TV, and secure parking.
Stylish & Spacious 3 Br~close To Battery Plant - Windsor
9.2 58 reviews
Windsor
20/07 – 21/08
A$100/nighttotal: A$3200 (32 )

Stylish & Spacious 3 Br~close To Battery Plant

3 2
apartment , Windsor
This apartment is situated in a peaceful neighbourhood in Windsor, just across from the Detroit River, 3km from Standpoint Beach and a short walk from the Ganachio Trail. The property has received excellent ratings for location, cleanliness, and user experience.
This three-bedroom flat comfortably sleeps six guests and features an open-plan kitchen, dining area, and living room. The apartment includes amenities such as a fridge, freezer, microwave oven, dishwasher, air conditioning, parking, and electronic keypad entry, making it a convenient choice for travellers.
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