Holiday Rentals in Windsor

1448 available vacation rental offers

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Windsor holiday rentals
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Windsor holiday rentals: compare the best deals

Best family friendly Windsor holiday rentals

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

3 Br Modern Home In Windsor (West) By The Bridge - Windsor
10 5 reviews
Windsor
06/30 – 07/02
HK$1332/nighttotal: HK$2664 (2 )

3 Br Modern Home In Windsor (West) By The Bridge

3 6
apartment , Windsor
This family-friendly apartment is located in the historic Sandwich Town district of Windsor, offering easy access to local cafes, restaurants, and the riverfront within 500 metres, and is a short drive to Windsor and Detroit.
This modern duplex accommodates up to six guests across three bedrooms, featuring air conditioning, a fully equipped kitchen, and private televisions in each room, with free street parking available nearby.
Full House, 3 Bdr, 2wr, Free Parking , Extra Beds - Windsor
9.7 50 reviews
Windsor
06/28 – 07/31
HK$818/nighttotal: HK$26994 (33 )

Full House, 3 Bdr, 2wr, Free Parking , Extra Beds

1 2
apartment , Windsor
This three-bedroom Windsor apartment, near EC Row, offers convenient access to the Ambassador Bridge (approx. 16km) and the US border (approx. 24km), plus easy reach of the University of Windsor (approx. 13km), shopping malls, and Costco.
The self-contained property features a fully equipped kitchen, private garden, parking, and sleeps four guests comfortably in queen-sized beds; a dedicated workspace and smart lock add convenience.
3br Modern & Spacious Downtown Apartment - Windsor
9.6 5 reviews
Windsor
10/01 – 12/31
HK$4997/nighttotal: HK$454727 (91 )

3br Modern & Spacious Downtown Apartment

3 3
apartment , Detroit
This former savings bank conversion in Downtown Detroit offers historic character and city views, situated a 1-7 minute walk from Eatóri Market, Dessert Oasis Coffee Roasters, La Lanterna, and within easy reach of the Fox Theatre and Comerica Park.
This spacious 130 square metre flat accommodates up to six guests across three bedrooms, featuring a Master Suite and two Guest Bedrooms with King Beds plus a Queen floor mattress, all equipped with individually controlled air conditioning, a washer/dryer, high-speed internet, and access to a rooftop terrace.
420 Friendly Spacious Corktown Loft Near Downtown Detroit - Windsor
Windsor
07/13 – 08/17
HK$1026/nighttotal: HK$35910 (35 )

420 Friendly Spacious Corktown Loft Near Downtown Detroit

1 2
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.

Best Windsor holiday rentals with parking

Modern Downtown Apartment - Windsor
8.6 18 reviews
Windsor
06/27 – 07/04
HK$4967/nighttotal: HK$34769 (7 )

Modern Downtown Apartment

1 2
apartment , Detroit
This Downtown Detroit flat is ideally located less than 1 km from Campus Martius Park, the Greektown Casino, and Comerica Park, with Ford Field and Little Caesars Arena within a 2.4 km radius.
The self-catering apartment offers two bathrooms, a washer/dryer, free Wi-Fi, and on-site parking, along with a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
Perfect For Groups Big Granite Island 5-star Stay - Windsor
10 20 reviews
Windsor
10/01 – 12/31
HK$1185/nighttotal: HK$107835 (91 )

Perfect For Groups Big Granite Island 5-star Stay

1 3
apartment , Windsor
This Windsor apartment boasts a prime location near the Aquatic Centre, a six-minute walk (approximately 0.4km) from the Capitol Theatre, and close proximity to the Detroit-Windsor Tunnel and Caesars Windsor.
The three-bedroom flat, sleeping up to six guests, offers a fully equipped kitchen, in-unit laundry, a patio with seating, and stunning Detroit skyline views; nearby attractions include the Windsor International Film Festival (at the Capitol Theatre).
7br House 19 Ppl Dt Windsor Wd Free Parking - Windsor
10 2 reviews
Windsor
08/02 – 08/05
HK$4476/nighttotal: HK$13428 (3 )

7br House 19 Ppl Dt Windsor Wd Free Parking

7 2
house , Windsor
This seven-bedroom house is located in the heart of Windsor, just 3.5 kilometres from the TCF Center, 3 kilometres from GM World, and 3.2 kilometres from Saint Andrews Hall. It has received excellent ratings for its location, cleanliness, and user experience.
The property has a floor area of 30 square metres and can comfortably accommodate up to 16 guests. Amenities include free parking, a non-smoking environment, and convenient access to Windsor International Airport, just 9 kilometres away.
Cozy 1 Bed Basement Studio Apt 10 Min To Downtown And Riverside - Windsor
8.0 2 reviews
Windsor
06/27 – 06/28
HK$902/nightfor 1 night

Cozy 1 Bed Basement Studio Apt 10 Min To Downtown And Riverside

1 2
studio , Windsor
This Forest Glade house, located 3.5km from the Windsor Family Credit Union Centre, offers easy access to Coventry Gardens and Lake St. Clair (both within 9.6km), and Detroit attractions such as the Detroit-Windsor Tunnel and Caesars Windsor (within 14.5km).
The one-bedroom, one-bathroom property sleeps two guests and includes a fireplace, Smart TV, microwave, free parking, and essential bathroom amenities; enjoy a smoke-free environment and explore nearby attractions.

Frequently asked questions about holiday rentals in Windsor

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

    For a first-time visit, you'd want to check out the iconic Windsor Sculpture Park, with its impressive collection of modern art. Don't miss the chance to explore the historic Fort Malden National Historic Site, offering a glimpse into the region's rich past.
  • What are the best Airbnb and vacation rentals in Windsor?

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

    The Olde Walkerville neighbourhood is a popular choice for vacation rentals. It's known for its charming Victorian architecture, lively restaurants, and proximity to the Detroit River.
  • What are the most popular Airbnbs in Windsor?

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

    Booking your vacation rental in advance is always recommended, especially during peak seasons like summer and the autumn months. You'll have a wider selection and potentially better prices.
  • What are the best vacation rentals with a pool in Windsor?

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

    The annual Windsor International Film Festival in November is a highlight, showcasing independent films. In June, the Windsor International Blues Festival brings live music and a vibrant atmosphere to the city.
  • What are the best rentals for families and kids in Windsor?

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

    A stroll along the scenic Detroit River Walk is a great free activity, offering beautiful views and fresh air. The Windsor Public Library is another budget-friendly option, hosting free events and providing access to books and resources.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

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

    For a taste of local cuisine, try The Twisted Apron, known for its innovative dishes featuring fresh, seasonal ingredients. The Old Stone Tavern offers a traditional pub atmosphere and classic comfort food.
  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a popular choice for both walking and cycling, offering stunning views of the Detroit River. The University of Windsor campus also has a network of well-maintained walking and cycling paths.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    The Windsor Sculpture Park welcomes well-behaved dogs on leash. The Detroit River Walk is also a great option for a stroll with your furry friend.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens and laundry facilities, making them a convenient option for families or longer stays.
  • 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. For outdoor activities, Dieppe Park offers a range of sports facilities, including tennis courts and a baseball diamond.

Destinations nearby

Best Windsor holiday rentals with a balcony

Cozy Detroit House - Balcony, Movie Yard, Fire Pit - Windsor
10 3 reviews
Windsor
10/03 – 10/07
HK$3286/nighttotal: HK$13144 (4 )

Cozy Detroit House - Balcony, Movie Yard, Fire Pit

3 2
apartment , Detroit
This spacious three-bedroom flat is situated in Detroit's North Corktown district, offering convenient access to the Fox Theatre and Henry Ford Museum, and a short distance to Ford Field and Little Caesars Arena.
This family-friendly residence accommodates up to eight guests and features a modern kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, parking, and an electric fireplace.
Three Bedroom Three Bath Penthouse With Sauna & Exercise/office Space - Windsor
9.0 23 reviews
Windsor
10/01 – 12/31
HK$1195/nighttotal: HK$108745 (91 )

Three Bedroom Three Bath Penthouse With Sauna & Exercise/office Space

3 3
apartment , Windsor
This apartment is located in the University district of Windsor, just 3km from the Detroit Windsor Tunnel and 2km from the Ambassador Bridge. The surrounding area is lively and offers a variety of restaurants and shops.
This self-catering property has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. It features a private pool, a hot tub, a sauna and a terrace, perfect for relaxing after a day of exploring.
New 10-18ft Ceilings Townhome-3 Bed With 3 Ensuite Baths - Windsor
Windsor
09/01 – 12/18
HK$1133/nighttotal: HK$122364 (108 )

New 10-18ft Ceilings Townhome-3 Bed With 3 Ensuite Baths

3 1
apartment , Windsor
This house is located in the University district of Windsor, just 4 kilometres from the Detroit Windsor Tunnel and 3 kilometres from the Ambassador Bridge, making it easy to explore both Windsor and Detroit. The neighbourhood is a lively and vibrant area, with a mix of residential and commercial properties.
This house offers 3 bedrooms and 3 bathrooms, comfortably accommodating up to 6 guests. The house is fully equipped with modern amenities, including air conditioning, a smart TV, Wi-Fi, a fully equipped kitchen, a washing machine and dryer, and a comfortable living area.
Perfect Getaway In Corktown! - Windsor
8.8 17 reviews
Windsor
07/30 – 08/30
HK$1218/nighttotal: HK$37758 (31 )

Perfect Getaway In Corktown!

1 2
apartment , Detroit
This stylish one-bedroom apartment is located in Detroit's Corktown district, less than 0.5 kilometres from Michigan Central Station, Comerica Park, Ford Field, and Little Caesars Arena.
The 111 square metre property features two bathrooms, a terrace, parking, a fully equipped kitchen including a dishwasher, and can comfortably accommodate three guests, with nearby access to various recreational activities including jet skiing and cycling.

Best Windsor holiday rentals with air conditioning

Homey Waterfront Townhouse, Skyline Views - Windsor
9.6 14 reviews
Windsor
06/27 – 07/04
HK$934/nighttotal: HK$6538 (7 )

Homey Waterfront Townhouse, Skyline Views

2 2
apartment , Windsor
This Windsor city-centre apartment is located minutes from Caesars Windsor, The Keg Steakhouse + Bar, and the Ambassador Bridge, offering easy access to downtown attractions.
The two-bedroom flat sleeps four, features a fully equipped kitchen, air conditioning, parking, and a shared laundry, boasting stunning Detroit skyline and river views.
Executive 2br | Fast Wifi +Parking | Near Tunnel - Windsor
9.7 37 reviews
Windsor
09/01 – 12/18
HK$850/nighttotal: HK$91800 (108 )

Executive 2br | Fast Wifi +Parking | Near Tunnel

2 1
apartment , Windsor
This apartment is situated in downtown Windsor, just a few hundred metres from the Windsor-Detroit Tunnel, making it a great choice for travellers crossing the border. It boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. This two-bedroom flat comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher. The apartment also has air conditioning, a garden, parking, and internet access, making it perfect for a relaxing and convenient stay in Windsor.
2-bedroom Apartment With Fast Wi-fi, Private Laundry & Entrance; Free Parking - Windsor
Windsor
06/28 – 07/31
HK$560/nighttotal: HK$18480 (33 )

2-bedroom Apartment With Fast Wi-fi, Private Laundry & Entrance; Free Parking

2 2
apartment , Windsor
This Windsor apartment rental in the Walkerville district offers convenient proximity to the Fox Theatre and Henry Ford Museum of American Innovation, with easy access to the Detroit-Windsor Tunnel and Ambassador Bridge.
The two-bedroom, one-bathroom flat sleeps four guests and includes in-unit laundry, a fully equipped kitchen, air-conditioned bedrooms with TVs, free Wi-Fi, and business amenities such as desks, office chairs, and a printer; free street parking is also available.
Newly Renovated 3 Bedroom Unit - Windsor
10 2 reviews
Windsor
07/30 – 08/30
HK$650/nighttotal: HK$20150 (31 )

Newly Renovated 3 Bedroom Unit

1 3
apartment , Windsor
This three-bedroom Windsor city centre flat is situated a short walk from the Riverfront, Caesar's Windsor, and the 5.17km Riverfront Trail.
The newly renovated apartment, sleeping five guests, boasts a kitchen with a fridge, air conditioning, internet access, and is pet-friendly; nearby attractions include Adventure Bay Family Water Park and a local grade school.
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