Vacation Rentals in Windsor

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Windsor holiday rentals
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2034 Holiday rentals and Airbnb in Windsor

Select Top Kid-Friendly Holiday Rentals in Windsor

Give everyone their own room to relax after a long day of sightseeing at spacious family holiday rentals in Windsor.

Hot Tub, Walk To Caesars, Free Parking, Sleeps 8 - Windsor
10 1 review

Hot Tub, Walk To Caesars, Free Parking, Sleeps 8

house, Windsor
This Windsor lodging is located just over 2.8 kilometres from Gm World, offering convenient access to downtown Detroit attractions including Caesars and the TCF Center.
This family-friendly dwelling provides accommodation for up to 8 guests across 2 bedrooms, featuring a fully equipped kitchen with a dishwasher, air conditioning, a hot tub, and free WiFi, with free parking also available.
The Victorian On Victoria - Windsor
9.6 30 reviews

The Victorian On Victoria

apartment, Windsor
This Victorian manor house in Windsor is centrally located, within walking distance of the Windsor Aquatic Centre and Chrysler Theatre, and a short drive (approximately 2km) from the Windsor-Detroit Tunnel and the Olde Walkerville district.
Offering three bedrooms sleeping seven, two bathrooms, a fully equipped kitchen, a private garden with swim spa (extra charge), high-speed internet, and gated parking for two cars, this Windsor property is perfect for families or groups.
Brand New Riverside Retreat | Stylish 2br +Parking - Windsor
10 55 reviews

Brand New Riverside Retreat | Stylish 2br +Parking

apartment, Windsor
This luxury apartment is conveniently located just off Riverside Drive in Windsor, placing you within easy reach of the city centre and its attractions, including the Detroit-Windsor Tunnel, just 2km away. Guests consistently rate the apartment as excellent for its location, cleanliness, and overall experience.
The apartment is ideal for families or groups of up to four, featuring two queen-sized beds and a well-equipped kitchen. Enjoy high-end amenities like a Jacuzzi, a private garden, and air conditioning, ensuring a comfortable and relaxing stay.
Charming Suite With Cozy Amenities - Serene Getaway For All - Windsor
No reviews

Charming Suite With Cozy Amenities - Serene Getaway For All

apartment, Windsor
This one-bedroom flat is situated in Walkerville, Windsor, offering convenient access within 10-15 kilometres to Windsor University, NextStar Energy, Flex-Ion Battery Plant, and the Ford Plant.
This residence accommodates up to three guests and features a fully equipped kitchen, a living area with a sofa bed and smart TV, in-suite laundry, and high-speed internet, with parking and air conditioning provided.

Best Windsor holiday rentals with parking

Cozy 2-bedroom Home W/ Modern Amenities In Windsor - Windsor
9.6 16 reviews

Cozy 2-bedroom Home W/ Modern Amenities In Windsor

apartment, Windsor
This Windsor self-catering apartment, located on Shadetree Crescent, offers convenient access to local attractions, though precise distances are not specified.
The two-bedroom, two-bathroom property sleeps four guests and includes a fully equipped kitchen with dishwasher, free Wi-Fi, and on-site parking (shared).
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.
2br Near Walkerville | Steps To Dining & Transit - Windsor
9.3 49 reviews

2br Near Walkerville | Steps To Dining & Transit

apartment, Windsor
This Walkerville flat is conveniently located less than a kilometre from Windsor's Via Rail station and Riverside Drive, offering easy access to shops, restaurants, and public transport (Transit Windsor Crosstown 2 bus stop).
The two-bedroom, one-bathroom apartment sleeps four, features a fully equipped kitchen, air conditioning, parking, and excellent guest reviews; nearby recreational opportunities along Riverside Drive enhance the stay.
Walkerville 1br Suite + Office | Near Casino & Ford - Windsor
No reviews

Walkerville 1br Suite + Office | Near Casino & Ford

apartment, Windsor
This Walkerville flat offers a convenient base in Windsor, situated 5 kilometres from Caesars Windsor Casino and downtown Windsor, and a 15-minute drive from major employers including Ford Motor Company and NextStar Energy.
This pet-friendly apartment for two features a fully equipped kitchen with a fridge and microwave, air conditioning, dedicated workspace, 50-inch Smart TV, secure keypad entry, high-speed Wi-Fi, and free nearby street parking.

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.

Popular destinations

Find Holiday Rentals with Balconies in Windsor

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Windsor.

Cozy 4 Bedroom Home Near Tecumseh Mall - Windsor
No reviews

Cozy 4 Bedroom Home Near Tecumseh Mall

house, Windsor
This four-bedroom detached house is located in Windsor, offering convenient access to Tecumseh Mall and being just 5 kilometres from Windsor International Airport, with major Detroit attractions such as the TCF Centre and GM World approximately 11 kilometres away.
This spacious property, covering 102 square metres, accommodates up to 11 guests with four bedrooms and two bathrooms, featuring a fully equipped kitchen including a microwave oven and coffee machine, free WiFi, a fireplace, and outdoor spaces like a balcony and patio.
Spacious Cheerful Home With 2 Free Parking - Windsor
No reviews

Spacious Cheerful Home With 2 Free Parking

cottage, Windsor
This charming cottage is situated in Bridgeview, Windsor, just a short walk from the University of Windsor and the Toldo Lancer Centre, making it ideal for exploring the city. The cottage is conveniently located near the U.S. Port of Entry, allowing easy access to both Canada and the United States.
The cottage offers two bedrooms and one bathroom, comfortably accommodating up to two guests. It features a fully equipped kitchen, a private garden with a double deck balcony, and a dedicated exercise area in the basement.
Modern 2br  Gated Parking  10 Min To Downtown - Windsor
No reviews

Modern 2br Gated Parking 10 Min To Downtown

apartment, Detroit
This renovated 2-bedroom flat is situated in Detroit, just over 1.6 kilometres from the city centre and a short distance from landmarks such as the Fox Theatre and the Henry Ford Museum.
This family-friendly duplex offers free gated parking, high-speed Wi-Fi, a full kitchen with fridge and microwave, an in-unit washer/dryer, Smart TVs, and a private entrance, providing convenient access to attractions like the Ambassador Bridge and the Detroit Zoo.
Downtown Detroit Modern Loft W/free Parking 420 - Windsor
9.5 294 reviews

Downtown Detroit Modern Loft W/free Parking 420

apartment, Detroit
This one-bedroom apartment is located in Corktown, a historic Detroit neighbourhood, just 1.5km from the Detroit Riverwalk, Huntington Place, and the People Mover. It has excellent user, location, and cleanliness ratings.
The apartment offers 93 square metres of space, accommodating up to three guests. It features a fully equipped kitchen, a private balcony, a tennis court, and a spa, as well as free Wi-Fi and a washing machine.

Best Windsor holiday rentals with air conditioning

Sleeps 8 | Bbq + Parking | Family Friendly - Windsor
9.8 11 reviews

Sleeps 8 | Bbq + Parking | Family Friendly

apartment, Windsor
This four-bedroom flat is situated in Windsor's Little Italy district, a short walk from top-rated restaurants.
This accommodation offers space for eight guests with two bathrooms, a well-equipped kitchen, high-speed internet, air conditioning, and secure parking in a detached garage, with backyard access for relaxation and family activities.
Rare Find By The Riverside - Windsor
9.6 86 reviews

Rare Find By The Riverside

apartment, Windsor
This beachfront Windsor condo is located a short drive (approximately 1.6km) from the University of Windsor and the Ambassador Bridge, offering easy access to downtown Windsor (around 3.2km away).
The one-bedroom apartment sleeps three, boasting a king-size bed, an extra air mattress, ensuite laundry, a fully equipped kitchen including a dishwasher, and a balcony overlooking the beach with direct access and proximity to the riverside trail, plus secure parking and fishing opportunities nearby.
Cozy 2-bedroom Basement Suite Near Battery Plant - East Windsor - Windsor
No reviews

Cozy 2-bedroom Basement Suite Near Battery Plant - East Windsor

apartment, Windsor
This two-bedroom flat is situated in the East Riverside district of Windsor, providing easy access to the Detroit Windsor Tunnel and Ambassador Bridge, both less than 1 kilometre away.
This self-catering accommodation can host up to four guests and includes high-speed Wi-Fi, air conditioning, a Smart TV, and a washer/dryer, with free parking available.
4br New Home Extended Stay Work Ready | Parking - Windsor
8.7 20 reviews

4br New Home Extended Stay Work Ready | Parking

apartment, Windsor
This four-bedroom house is located in a welcoming neighbourhood, offering convenient access to Windsor's attractions.
This fully equipped residence accommodates up to eight guests, featuring king-sized beds, a modern kitchen with a dishwasher, air conditioning, and Wi-Fi, with parking available and pets welcomed.

Your Curated List of Premium Holiday Rentals in Windsor

Treat yourself to smart-home features, high-end interiors, and curated artwork at luxury holiday rentals in Windsor.

Luxury Condo Windsor/lasalle Ontario - Windsor
9.9 37 reviews

Luxury Condo Windsor/lasalle Ontario

apartment, Windsor

Find Holiday Rentals in the CBD of Windsor

Spend less time navigating public transport and more time exploring attractions from central holiday rentals in Windsor.

Bornu-2nd Flr Spacious, Location, Clean, 1bdr, A/c - Windsor
9.4 223 reviews

Bornu-2nd Flr Spacious, Location, Clean, 1bdr, A/c

apartment, Windsor
Walk To Caesars Casino Sleeps 8 Hot Tub 2 Parking - Windsor
9.5 24 reviews

Walk To Caesars Casino Sleeps 8 Hot Tub 2 Parking

apartment, Windsor
Modern 1 Br Granite Counters Near Casino & Tunnel - Windsor
9.9 97 reviews

Modern 1 Br Granite Counters Near Casino & Tunnel

apartment, Windsor
706# Cheapest Great Home, Walk To Casino Tunnel - Windsor
9.2 567 reviews

706# Cheapest Great Home, Walk To Casino Tunnel

apartment, Windsor
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