Holiday Rentals in Windsor

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Windsor holiday rentals
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2034 Holiday rentals and Airbnb in Windsor

Best family friendly Windsor holiday rentals

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

Beautiful Newly Designed Luxurious Apartment - Windsor
8.5 22 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.
Executive 2br Lower Suite Private & Spacious Close To Usa Border - Windsor
9.7 14 reviews

Executive 2br Lower Suite Private & Spacious Close To Usa Border

apartment, Windsor
This two-bedroom flat in Windsor is situated 9.4 kilometres from the TCF Centre and 8.8 kilometres from GM World, offering convenient access to Detroit landmarks.
This family-friendly apartment, covering 45 square metres, features two bedrooms, one bathroom with a bidet, air conditioning, free Wi-Fi, a kitchen with a fridge and microwave, and parking, accommodating up to 11 guests.
5 Star Hotel Inspired Home | Gym  Sauna  Arcades - Windsor
10 82 reviews

5 Star Hotel Inspired Home | Gym Sauna Arcades

apartment, Windsor
This two-bedroom house is situated in a desirable neighbourhood in Windsor, close to the 401 highway, the airport, St. Clair College, and Devonshire Mall. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This comfortable home offers a spacious and open concept layout, accommodating up to four guests. Enjoy a range of amenities including a fully equipped kitchen, air conditioning, a private garden, a sauna, and a fitness centre.
Detroit Loft Fort Pontchartrain - Windsor
10 1 review

Detroit Loft Fort Pontchartrain

apartment, Detroit
This two-bedroom flat is ideally located in Detroit, within a 3-5 kilometre radius of popular attractions like Saint Andrews Hall, GM World, Music Hall Center, and the TCF Center. The area offers a peaceful retreat from the city's hustle and bustle, while still being close to the action.
The 102 square metre flat comfortably accommodates up to five guests. It comes equipped with modern amenities including air conditioning, a flat-screen TV, a fully equipped kitchen, free Wi-Fi, and a garden.

Best Windsor holiday rentals with parking

1037 Assumption · Brand New 1-bedroom House By The Riverfront - Windsor
No reviews

1037 Assumption · Brand New 1-bedroom House By The Riverfront

apartment, Windsor
This Walkerville flat is located in Windsor, just 160 metres from the Detroit Riverfront Trail, offering views of Detroit's skyline and proximity to Assumption Church and the Olde Walkerville district.
This 88 square metre flat accommodates four guests, featuring a full kitchen, on-site parking, and is a short walk from Walkerville's restaurants, cafes, and shops.
Spacious 4-bedroom Historic House With Wifi In Heart Of Detroit/free Parking! - Windsor
8.6 4 reviews

Spacious 4-bedroom Historic House With Wifi In Heart Of Detroit/free Parking!

apartment, Detroit
This Detroit dwelling, ideally situated for exploring the city, offers easy access to attractions such as the Fox Theatre, Greenfield Village, and the Detroit Zoo, although precise distances aren't specified.
The four-bedroom, four-bathroom property sleeps up to 16 guests, boasting a fully fenced yard, modern amenities including WiFi and a dishwasher, and is perfect for families or large groups visiting the city's sporting and entertainment venues like Little Caesars Arena and Ford Field.
Zulu-1br, Queen+sofa Bed, Ac, Next To Tunnel To Us - Windsor
9.6 179 reviews

Zulu-1br, Queen+sofa Bed, Ac, Next To Tunnel To Us

apartment, Windsor
This apartment is situated in the heart of Windsor, just 0.5km from City Hall, 1km from the casino, Walkerville, the riverfront, and St. Clair Avenue, offering easy access to all the city's attractions. It has received consistently excellent ratings for its location, cleanliness, and overall experience.
The flat is a one-bedroom, one-bathroom apartment with a separate living room and kitchen, suitable for up to two guests. It is equipped with free parking, high-speed Wi-Fi, a fully equipped kitchen, and a comfortable queen bed, as well as a twin air mattress for a third guest.
5-acre-secluded-farm-detroit-swimmingpond-first-black-owned-cider-mill - Windsor
10 1 review

5-acre-secluded-farm-detroit-swimmingpond-first-black-owned-cider-mill

apartment, Detroit
This Detroit family-friendly farmhouse is located in an 11-minute walk from the Boston Edison Historic District and a short 4-minute drive (approximately 2.4km) from the Motown Museum.
Sleeping eight guests, this self-catering property boasts a bedroom, bathroom, well-equipped kitchen, swimming pool, tennis court, and BBQ, plus on-site kayak and bike rentals and proximity to attractions like the Fox Theatre and Detroit Zoo.

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

Charming Historic Home | Quiet Luxury + Backyard - Windsor
9.8 9 reviews

Charming Historic Home | Quiet Luxury + Backyard

apartment, Detroit
This Detroit holiday home is situated in Midtown, less than 1.6km from the Motown Museum and Henry Ford Hospital, offering easy access to major attractions.
The 178 square metre property boasts three bedrooms sleeping three guests, a fully equipped kitchen with appliances including a dishwasher, a private balcony, on-site laundry, and a peaceful garden.
Avelines Abode - N. Corktown - Windsor
10 29 reviews

Avelines Abode - N. Corktown

apartment, Detroit
This Detroit flat is situated in the North Corktown district, offering convenient access to attractions, with Little Caesars Arena and the historic Fox Theatre both a mere 3-minute drive away.
Spanning 124 square metres, this two-bedroom, two-bathroom apartment accommodates up to four guests and features a fully equipped kitchen, in-unit laundry, air conditioning, complimentary Wi-Fi, and on-site parking.
Alexandria's Motor City Condo Apartment - Windsor
9.8 18 reviews

Alexandria's Motor City Condo Apartment

apartment, Detroit
This refurbished 100-year-old upper unit condo in Detroit offers convenient access to major freeways and the airport, placing it within easy reach of landmarks such as the Detroit Windsor Tunnel, Greenfield Village, Fox Theatre, Comerica Park, and Little Caesars Arena.
Spanning 121 square meters, this family-friendly flat accommodates up to 4 guests with 3 bedrooms, a fully equipped kitchen featuring a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, parking, and a dedicated office space, all complemented by retained historical charm including a clawfoot tub.
Spacious Detroit Retreat  Sleeps 16  Parking - Windsor
8.8 3 reviews

Spacious Detroit Retreat Sleeps 16 Parking

apartment, Detroit
This six-bedroom Detroit dwelling, sleeping sixteen, is situated in the West Village, approximately 5 kilometres from Belle Isle and Eastern Market, and a short drive from the city centre.
The 500 sq ft master suite, three bathrooms, fully equipped kitchen, PS5, Ms Pac-Man arcade game, and three smart TVs are among the amenities in this spacious property, ideally suited for large families or groups.

Best Windsor holiday rentals with air conditioning

Turkey Creek Hideaway - Windsor
10 64 reviews

Turkey Creek Hideaway

apartment, Windsor
This charming house is located on a quiet street in Windsor, just a short walk from shops and restaurants, and backing onto Turkey Creek and nature trails. It has received excellent ratings for its location, cleanliness, and overall experience.
The property offers three bedrooms with unique themes, a modern kitchen, two living rooms, a dining room, and a bathroom with a full-sized bathtub and shower, comfortably accommodating up to six guests. Guests can enjoy a range of amenities, including a garden, a patio with a barbecue, fireplaces, and a selection of games, puzzles, and books for relaxation and entertainment.
Luxury 2br Home With High Ceilings And Bbq W/patio - Windsor
9.9 180 reviews

Luxury 2br Home With High Ceilings And Bbq W/patio

apartment, Windsor
This charming chalet is located in the EC Row district of Windsor, just 7 kilometres from the US border and downtown Windsor, offering a peaceful retreat from the city.
The chalet has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features modern amenities such as high-speed internet, two smart TVs with streaming services, and a fully equipped kitchen with a fridge, freezer, and microwave.
Frida's House - Windsor
No reviews

Frida's House

apartment, Detroit
This Frida Kahlo inspired Victorian residence in Detroit offers a unique artistic ambiance, featuring botanical murals and Spanish tile, with multiple gathering spaces including two living rooms and a vaulted attic lounge, located a short distance from downtown attractions and a 15-minute walk to Michigan Central Station.
This spacious seven-bedroom, three-bathroom flat accommodates up to 14 guests, boasting a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, parking, and sunrooms with hammocks, ideal for families seeking a distinctive stay.
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.
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