Holiday 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

Modern Stay W Granite Island & Detroit River Views - Windsor
10 15 reviews

Modern Stay W Granite Island & Detroit River Views

apartment, Windsor
This two-bedroom flat in downtown Windsor offers an excellent base, just 100 metres from the Detroit-Windsor Tunnel and Caesars Casino, with direct views of the Detroit skyline and riverfront.
This family-friendly apartment accommodates two guests and features air conditioning, a modern kitchen with a dishwasher, and secure gated parking, providing convenient access to local attractions like the Windsor International Aquatic and Training Centre and major Detroit venues via the tunnel bus service.
Historic Elegance Meets Modern Comfort|stylish 2br - Windsor
9.9 19 reviews

Historic Elegance Meets Modern Comfort|stylish 2br

apartment, Windsor
This renovated 1912 townhome is situated centrally in Walkerville, a historic district, offering proximity to dining and local attractions.
This pet-friendly two-bedroom, two-bathroom maisonette accommodates up to five guests and features a modern kitchen, air conditioning, a private garden with seating, and dedicated parking.
East Grand Marrakesh - Windsor
8.9 9 reviews

East Grand Marrakesh

apartment, Detroit
This one-bedroom apartment is conveniently located in Detroit, approximately 5 kilometres from the city centre, close to attractions such as the Gem Theatre, Music Hall Centre and St Andrew's Hall.
The 100 square metre flat offers a fully equipped kitchen, a walk-in shower and dressing room, free Wi-Fi, air conditioning and private parking, making it ideal for a family of up to three people.
Stylish High-rise Loft In Downtown Detroit | City Views - Windsor
No reviews

Stylish High-rise Loft In Downtown Detroit | City Views

apartment, Détroit
This Downtown Detroit flat offers immediate access to attractions such as Comerica Park and the Fox Theatre, with Grand Circus Park and Broadway metro stations just 500 meters away for convenient city exploration.
This 102 square meter residence accommodates up to six guests across three bedrooms and three bathrooms, featuring a fully equipped kitchen, air conditioning, on-site parking, and an in-unit washer and dryer.

Best Windsor holiday rentals with parking

Windsor Airport Accommodation Whole House - Windsor
9.5 20 reviews

Windsor Airport Accommodation Whole House

house, Windsor
This three-bedroom, two-bathroom Windsor apartment, ideal for families or groups of up to six, offers excellent cleanliness and location ratings, though its precise location within Windsor and proximity to specific landmarks such as Windsor Castle remains unspecified.
The self-catering property includes a kitchen, air conditioning, parking, and internet access; further details regarding the apartment's size, layout, and specific amenities are unavailable.
Modern 2br/2ba Retreat  2 Queen Beds With Parking - Windsor
9.3 14 reviews

Modern 2br/2ba Retreat 2 Queen Beds With Parking

apartment, Windsor
This modern two-bedroom flat in Windsor is situated just 500 metres from the Riverfront and Dieppe Gardens, offering convenient access to Caesars Windsor Casino, Devonshire Mall, and the University of Windsor.
This serviced apartment accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a fitness centre, and free Wi-Fi, making it ideal for those visiting the Essex County Wineries or Point Pelee National Park.
Modern 3br/2ba House - Windsor
9.8 10 reviews

Modern 3br/2ba House

apartment, Windsor
This Windsor duplex apartment, ideal for families, offers three bedrooms with double beds and smart TVs, two bathrooms, and sleeps six, conveniently located near Windsor's attractions, although precise distances aren't specified.
The property includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus Wi-Fi, air conditioning, parking, and an initial supply of consumables; additional linens and towels are available at extra cost.
The Painted House By Eastern Market ~Boutique B&b~ - Windsor
9.7 221 reviews

The Painted House By Eastern Market ~Boutique B&b~

cabin, Detroit
This modern home is located within a 1.5 kilometre walk of Eastern Market, Downtown Detroit, and the Detroit River, offering easy access to the city's key attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The house features a unique open floor plan designed by Cranbrook Architecture students, accommodating up to 10 guests. Amenities include a fully equipped kitchen, a private hot tub, a garden with fresh produce, and a sustainable design that maximises natural ventilation and minimises environmental impact.

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 spot for families, with plenty of space for kids to run around and lots of interesting sculptures to explore. The Ojibway Nature Centre is another popular choice, with nature trails, a butterfly garden, and a chance to see local wildlife.
  • 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, from April to May or September to October. You'll avoid the crowds and enjoy milder weather, plus prices are usually lower.
  • What are the most popular Airbnbs in Windsor?

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

    The Windsor International Film Festival is a big event in the city, showcasing films from around the world. The Windsor-Essex County Wine Festival is another popular event, offering the chance to sample wines from local vineyards.
  • What are the best holiday rentals with a pool in Windsor?

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

    A walk along the Detroit Riverfront is free and offers stunning views. The Windsor Public Library has free events and programs throughout the year, and the University of Windsor campus is a great place for a picnic and a stroll.
  • What are the best rentals for families and kids in Windsor?

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

    The Twisted Apron is a great spot for local cuisine, serving up fresh, seasonal dishes with a focus on regional ingredients. You can't go wrong with a classic Windsor burger from the legendary The Old Mill.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

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

    The Riverfront Trail is a popular choice for walkers and cyclists, offering scenic views of the Detroit River. For a more challenging ride, try the Ojibway Park trails, which wind through forests and wetlands.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    Yes, there are a number of pet-friendly attractions in Windsor. The Windsor Sculpture Park welcomes dogs on leashes, and many of the restaurants in the Olde Walkerville neighbourhood have outdoor patios that are dog-friendly.
  • 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 often come with amenities like a kitchen and laundry facilities. They can also be a more budget-friendly option, especially for families or groups.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    The WFCU Centre is a multi-purpose arena that hosts a variety of sporting events, including hockey, basketball, and concerts. The University of Windsor also has a number of athletic facilities, including a swimming pool, a fitness centre, and a track and field.

Popular destinations

Best Windsor holiday rentals with a balcony

The Bachelor Suite At Stanley/kitchenette&backyard - Windsor
No reviews

The Bachelor Suite At Stanley/kitchenette&backyard

apartment, Windsor
This Remington Park flat in Windsor offers a private patio overlooking a tranquil backyard, conveniently located near Devonshire Mall with easy access to Windsor city centre, the airport, and the US border crossings.
The self-contained apartment sleeps two, featuring a king-size bed and futon, a well-equipped kitchenette including an air fryer, a 32-inch LG Smart TV, and a dedicated workspace; proximity to attractions such as the Fox Theatre, the Detroit-Windsor Tunnel, and the Ambassador Bridge adds further appeal.
Near Midtown & Medical District! Updated Unit - Windsor
10 2 reviews

Near Midtown & Medical District! Updated Unit

apartment, Detroit
This Detroit flat is situated in the historic Northwest Goldberg district, offering swift access to I-94 and M-10, and is located 0.9 kilometres from the Motown Museum, 2 kilometres from Wayne State University, and 3 kilometres from downtown entertainment venues.
This 139 square metre dwelling accommodates six guests with three bedrooms and two bathrooms, featuring amenities such as a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace, garden, parking, and a bonus storage loft.
Cozy, Modern 2br W/ Remote Workspace, Patio & Gym - Windsor
No reviews

Cozy, Modern 2br W/ Remote Workspace, Patio & Gym

house, Windsor
This modern 3-bedroom detached house in Windsor is situated 3.06 kilometres from Windsor International Airport and within an 8.53-kilometre radius of the TCF Centre and Gm World.
This property offers accommodation for up to 11 guests with a floor area of 23 square metres, featuring a fully equipped kitchen, air conditioning, a private patio, a garden, an on-site gym, and dedicated remote workspace, with parking and Wi-Fi included.
Windsor Luxury Oasis - Windsor
10 4 reviews

Windsor Luxury Oasis

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.

Best Windsor holiday rentals with air conditioning

Charming Upper, 3bd, With Workspace In Walkerville - Windsor
9.5 15 reviews

Charming Upper, 3bd, With Workspace In Walkerville

apartment, Windsor
This Walkerville apartment, a short distance from Willistead Manor, offers a convenient location in Windsor.
The newly renovated three-bedroom property features a private entrance, street parking, a private laundry, high-speed internet, and can comfortably accommodate four guests.
The Parkside Lofts | Modern Studio With Style - Windsor
9.5 12 reviews

The Parkside Lofts | Modern Studio With Style

apartment, Windsor
This West Windsor studio apartment is situated a short distance from the University of Windsor and the waterfront, offering easy access to Windsor city centre.
The self-catering unit, sleeping up to two guests, includes a private kitchen with fridge, freezer, and microwave, a bathroom, in-unit laundry, and high-speed Wi-Fi; free parking is available.
Old Walkerville Main Floor 2bd/1ba - Windsor
No reviews

Old Walkerville Main Floor 2bd/1ba

apartment, Windsor
This two-bedroom flat is situated in Walkerville, Windsor, a short 8km drive from Windsor city centre, the Detroit-Windsor Tunnel, and conveniently located 1 minute from the VIA Rail station and 16km from Tecumseh, close to the Hiram Walker & Sons distillery and Walkerville Brewery.
The 84 square metre ground-floor property sleeps five, featuring a fully equipped kitchen with dishwasher, air conditioning, parking, high-speed internet, and access to shared amenities including a laundry, BBQ and picnic area; an air mattress is available on request.
Papa's Place Urban Cottage Retreat - Windsor
9.6 32 reviews

Papa's Place Urban Cottage Retreat

apartment, Detroit
Papa's Place is a centrally located flat in Detroit, just a 10-minute drive from the city centre and within walking distance of the Motown Museum, Dbads outdoor museum, and the New Centre Area. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom apartment comfortably sleeps four guests and is equipped with a modern kitchen, air conditioning, and a terrace or balcony. Enjoy the garden, parking, and internet access, along with the unique blend of historic charm and modern comfort this renovated 1913 home offers.
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