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

Detroit Riverview Loft - Windsor
Windsor
10/03 – 10/07
HK$1491/nightTotal: HK$5964 (4 )

Detroit Riverview Loft

1 2
apartment , Detroit
This Detroit Riverview Loft apartment is situated near the Detroit River, approximately 3.2 kilometres from Saint Andrew's Hall and 4 kilometres from the TCF Center.
This 98-square-metre flat offers one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, garden access, on-site parking (at an extra cost), and amenities such as a fireplace, washing machine, and access to billiards and darts.
Close To Downtown Ford Field/little Caesars - Windsor
9.8 35 reviews
Windsor
07/17 – 07/19
HK$2803/nightTotal: HK$5606 (2 )

Close To Downtown Ford Field/little Caesars

1 8
apartment , Detroit
This Detroit flat is situated in a lively neighbourhood just 5 kilometres from the city centre, offering easy access to a range of restaurants and bars. It has excellent user, location, and cleanliness ratings.
The three-bedroom property can accommodate up to eight guests and features a fully equipped kitchen, a private outdoor space, and modern amenities including high-speed internet and a smart TV. Guests can also enjoy the convenience of free parking and a nearby bike share station.
Spacious 4br Little Italy Retreat - Windsor
Windsor
09/01 – 12/18
HK$1366/nightTotal: HK$147528 (108 )

Spacious 4br Little Italy Retreat

4 1
apartment , Windsor
This centrally located flat in Windsor offers excellent access to the Detroit Windsor Tunnel, situated just 200 meters away, and is within easy reach of downtown attractions.
This stylish apartment accommodates up to 8 guests, featuring 2 bathrooms, a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, and on-site parking, with small pets permitted for an additional fee.
New 3br Stylish Downtown Suite - Windsor
Windsor
09/01 – 12/18
HK$4691/nightTotal: HK$506628 (108 )

New 3br Stylish Downtown Suite

3 1
apartment , Detroit
This downtown Detroit flat is a 5-minute walk from Campus Martius Park and the Guardian Building, with easy access to the Campus Martius streetcar and Cadillac Centre metro station.
This family-friendly accommodation offers 130 square metres of space with 3 bedrooms and 2 bathrooms, sleeping up to 6 guests, and features a fully equipped kitchen, Wi-Fi, and in-unit laundry.

Best Windsor holiday rentals with parking

Lumber Barons Brush Park Penthouse - 3br - 2 Kings/queen/2.5bath - 1-car Garage - Windsor
9.8 40 reviews
Windsor
06/27 – 06/28
HK$8730/nightfor 1 night

Lumber Barons Brush Park Penthouse - 3br - 2 Kings/queen/2.5bath - 1-car Garage

3 2
apartment , Detroit
This apartment is situated on the top floor of a restored historic mansion in the Brush Park neighbourhood of Detroit, just a short walk from the Detroit Institute of Arts, Comerica Park, Little Caesars Arena, and the Fox Theatre. It has received excellent reviews from previous guests.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace, and parking, as well as free internet access and multiple TVs with streaming services.
Elegant Detroit Home, 1br/1ba Near Downtown, Parks, Dining And Culture Vibes - Windsor
10 1 review
Windsor
07/30 – 08/30
HK$839/nightTotal: HK$26009 (31 )

Elegant Detroit Home, 1br/1ba Near Downtown, Parks, Dining And Culture Vibes

1 3
apartment , Detroit
This one-bedroom flat is situated in Detroit's historic Woodbridge district, providing easy access to cultural sites such as the Fox Theatre and Greenfield Village, and entertainment hubs including Little Caesars Arena and Comerica Park.
This 139 square metre residence accommodates up to four guests and includes a kitchen with a fridge, microwave, and dishwasher, alongside air conditioning and a garden, with parking available.
2 Bedroom Cozy Accommodation - Windsor
8.6 5 reviews
Windsor
11/16 – 12/07
HK$411/nightTotal: HK$8631 (21 )

2 Bedroom Cozy Accommodation

1 4
apartment , Windsor
This two-bedroom flat in Windsor is located approximately 8.4 kilometres from Detroit landmarks including the TCF Centre, GM World, Saint Andrew's Hall, the Gem Theatre, and the Music Hall Centre.
This 600 square meter flat offers air conditioning, complimentary WiFi, a kitchen with a fridge and microwave, and a garden, with parking available and pets welcome, accommodating up to seven guests.
Beautiful And Elegant Executive Rental For Longer Term Stays. 2 Br, 2 Bath. - Windsor
Windsor
07/01 – 01/01
HK$908/nightTotal: HK$167072 (184 )

Beautiful And Elegant Executive Rental For Longer Term Stays. 2 Br, 2 Bath.

2 2
apartment , Windsor
This two-bedroom, two-bathroom apartment is situated in Riverside, just 2.6 kilometres from the Windsor Family Credit Union Centre and within 10 kilometres of the Detroit Windsor Tunnel and Coventry Gardens. The surrounding neighbourhood is quiet and offers easy access to the Windsor Family Credit Union Centre, the Detroit Windsor Tunnel, and other attractions.
The apartment features a kitchen with an island, providing a comfortable and spacious setting for travellers. Amenities include free Wi-Fi, a smart TV, parking, and a smoke-free environment.

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

Three Bedroom Three Bath Penthouse With Sauna & Exercise/office Space - Windsor
9.0 23 reviews
Windsor
10/01 – 12/31
HK$1198/nightTotal: HK$109018 (91 )

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

3 2
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.
7br House 19 Ppl Dt Windsor Wd Free Parking - Windsor
10 2 reviews
Windsor
07/25 – 07/26
HK$9694/nightfor 1 night

7br House 19 Ppl Dt Windsor Wd Free Parking

7 4
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.
Modern & Stylish 4br Home - Near Detroit Downtown - Sleeps 10 - Pet-friendly - Windsor
10 4 reviews
Windsor
06/30 – 07/02
HK$3892/nightTotal: HK$7784 (2 )

Modern & Stylish 4br Home - Near Detroit Downtown - Sleeps 10 - Pet-friendly

4 6
apartment , Detroit
This four-bedroom, three-and-a-half-bathroom house is located in Detroit's Islandview neighbourhood, a short 4km drive from Belle Isle Park and approximately 7km from Comerica Park and Ford Field.
The spacious three-storey property sleeps ten guests and boasts a chef's kitchen, multiple living areas, a third-floor loft with vaulted ceilings, a private balcony from the master suite, a designated pet area, and driveway parking, alongside family-friendly amenities including a high chair and crib.
Windsor Luxury Oasis - Windsor
10 3 reviews
Windsor
11/16 – 12/07
HK$3695/nightTotal: HK$77595 (21 )

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.

Best Windsor holiday rentals with air conditioning

"Ethel's Place", Canada - Windsor
10 71 reviews
Windsor
06/27 – 07/04
HK$1134/nightTotal: HK$7938 (7 )

"Ethel's Place", Canada

1 2
apartment , Windsor
This Airbnb apartment is conveniently located on the main floor of a duplex in Windsor, just a short drive from the waterfront and the city centre. The apartment has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is spacious and comfortable, comfortably accommodating up to four guests. The apartment is fully furnished with modern kitchen appliances and laundry facilities, a private garden, and free parking on-site.
The Serene Walkerville Stay - Windsor
10 10 reviews
Windsor
07/25 – 10/31
HK$760/nightTotal: HK$74480 (98 )

The Serene Walkerville Stay

1 1
apartment , Windsor
This one-bedroom apartment in Walkerville, Windsor, is conveniently located within a 15-minute drive (approx. 10-15km) of the University of Windsor, Caesars Windsor, and the Windsor Airport.
The self-catering flat offers parking, Wi-Fi, air conditioning, and sleeps up to four guests, with easy access to major employers including NextStar Energy and the Ford Plant.
Stylish 2-bedroom Apartment In Downtown Windsor - Windsor
8.8 32 reviews
Windsor
12/15 – 12/28
HK$920/nightTotal: HK$11960 (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.
Chagga- 1br Clean-quiet Aptmt-location-rain Shower - Windsor
8.8 59 reviews
Windsor
06/29 – 07/13
HK$395/nightTotal: HK$5530 (14 )

Chagga- 1br Clean-quiet Aptmt-location-rain Shower

1 1
apartment , Windsor
This Windsor city centre flat offers exceptionally central accommodation, a one-minute walk from the Detroit–Windsor Tunnel and within 1.6km of Windsor City Hall, the casino, the riverfront, and Walkerville.
The one-bedroom apartment sleeps two, includes a fridge, freezer, microwave, free parking, and air conditioning, boasting a modern interior and a recently installed solid wood door for added security.
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