Holiday Rentals in Windsor

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Windsor holiday rentals
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Best Holiday rentals and Airbnb offers in Windsor

Explore Holiday Rentals for Families in Windsor

Travelling to Windsor with children? A quality family holiday rental or Airbnb makes everything easier with city attractions nearby.

Stylish House In South Windsor-2 Bedrooms - Windsor
9.4 183 reviews
Windsor
25/07 – 26/07
£87/nightfor 1 night

Stylish House In South Windsor-2 Bedrooms

1 4
apartment , Windsor
This recently renovated two-bedroom house is situated in South Windsor, just 5 kilometres from the Ambassador Bridge and 10 kilometres from the new bridge, offering easy access to both Canada and the United States. The property features a fully equipped kitchen, air conditioning, parking, and can comfortably accommodate up to four guests, making it ideal for families or groups of friends exploring Windsor.
The Windsor Mainstay - Windsor
Windsor
26/06 – 18/07
£85/nighttotal: £1870 (22 )

The Windsor Mainstay

2 4
apartment , Windsor
The Windsor Mainstay, a family-friendly flat, offers convenient access to Detroit attractions, with the TCF Centre located 5.3 kilometres away and GM World 4.7 kilometres away.
This apartment provides complimentary private parking, high-speed WiFi, air conditioning, and a well-equipped kitchen featuring a microwave oven, making it ideal for travellers seeking comfortable accommodation in Windsor.
3 Br Modern Home In Windsor (West) By The Bridge - Windsor
10 5 reviews
Windsor
25/06 – 27/06
£115/nighttotal: £230 (2 )

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

3 5
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.
Large Quiet Estate Property In Beautiful Natural Surroundings. - Windsor
9.8 126 reviews
Windsor
10/08 – 16/08
£696/nighttotal: £4176 (6 )

Large Quiet Estate Property In Beautiful Natural Surroundings.

6 2
apartment , Windsor
This luxurious home is situated on Windsor's finest golf course, just minutes from the Ambassador Bridge connecting to Detroit, Michigan, offering scenic views and a peaceful atmosphere. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious six-bedroom property is beautifully furnished and designed, providing ample space for large groups or families. The home offers a private pool, hot tub, yoga room, outdoor kitchen and bar, and full access to the estate, creating a resort-like experience.

Popular Holiday Rentals with Parking in Windsor

Park up and enjoy the city centre. These holiday rentals in Windsor come with a free car park on-site. Start comparing now.

Unique 2-bdr Historic Warehouse Loft With Terrace And Fireplace ! ! ! - Windsor
10 7 reviews
Windsor
27/06 – 28/06
£249/nightfor 1 night

Unique 2-bdr Historic Warehouse Loft With Terrace And Fireplace ! ! !

2 2
apartment , Windsor
This Windsor city-centre apartment, located 0.7km from Caesars Windsor and offering Detroit skyline views, resides in a historic early 1900s former prohibition-era factory building near the Walkerville district.
The 102 square metre flat features two bedrooms, one bathroom, sleeps five, and includes a terrace, garden, parking, internet access, air conditioning, and a kitchen equipped with a fridge and microwave.
Private Clean Suite Getaway |Work & Relax In Style - Windsor
9.7 50 reviews
Windsor
26/09 – 28/09
£89/nighttotal: £178 (2 )

Private Clean Suite Getaway |Work & Relax In Style

1 2
apartment , Windsor
This private, self-contained flat, situated near Seminole Street in Windsor, offers excellent access to local amenities and is a short walk from Ford Test Park.
This modern one-bedroom flat for two guests boasts a dedicated workspace, a fully equipped kitchen with a dishwasher and washer/dryer, and entertainment options including a PS5 and premium streaming services, all complemented by high-speed internet and air conditioning.
Papa's Place Urban Cottage Retreat - Windsor
9.7 29 reviews
Windsor
03/07 – 05/07
£193/nighttotal: £386 (2 )

Papa's Place Urban Cottage Retreat

2 2
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.
Downtown Detroit Gem- Walking Distance From Arenas And Stadiums! - Windsor
Windsor
04/07 – 05/07
£213/nightfor 1 night

Downtown Detroit Gem- Walking Distance From Arenas And Stadiums!

1 2
apartment , Detroit
This Brush Park flat offers proximity to Detroit's key attractions, being a short walk from Comerica Park and Little Caesars Arena, and close to the Fox Theatre and Detroit Windsor Tunnel.
This one-bedroom flat, accommodating up to three guests, features a queen bed and futon, a bathroom with a bath, and essential amenities including air conditioning and Wi-Fi, making it suitable for leisure and business trips.

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 should definitely check out the Windsor Sculpture Park, a free outdoor gallery with fascinating contemporary sculptures. You can also visit the Ojibway Nature Centre, a beautiful natural area with walking trails, a butterfly garden, and a nature centre.
  • What are the best Airbnb and holiday rentals in Windsor?

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

    The Walkerville neighbourhood is a great choice for a vacation rental. It's a historic district with charming Victorian architecture, trendy restaurants, and art galleries. It's also close to the Detroit River and the downtown core.
  • What are the most popular Airbnbs in Windsor?

  • What are the top family-friendly attractions in Windsor, Ontàrio, Canadà?

    For families, the Windsor Sculpture Park is a great place to visit. There's also the Chimczuk Museum, which has interactive exhibits on science and technology. And for a fun day out, you can visit the Adventure Bay Family Waterpark, a large water park with slides, pools, and a wave pool.
  • What are the best holiday rentals with a pool 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 and September to October. You'll find better deals on rentals and fewer crowds, but you'll still be able to enjoy the pleasant weather.
  • What are the best rentals for families and kids in Windsor?

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

    The Windsor International Film Festival is a great event to catch in late November, showcasing a range of films from around the world. In the summer, there's the Windsor International Jazz Festival, featuring live music performances from local and international artists.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

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

    For a budget-friendly activity, take a stroll along the Detroit Riverfront. You can also visit the Windsor Sculpture Park, which is free to enter. If you're looking for a unique experience, visit the Art Gallery of Windsor, which offers free admission on the first Sunday of every month.
  • What are the best restaurants with local dishes in Windsor, Ontàrio, Canadà?

    For a taste of local cuisine, check out The Twisted Apron, a popular restaurant known for its fresh, locally sourced ingredients. Another great option is The Colosseum, a classic Italian restaurant that's been serving Windsor for over 50 years.
  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a popular walking and cycling route that runs along the Detroit River. You can also explore the trails at the Ojibway Nature Centre, which offer stunning views of the natural landscape.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    Yes, there are several pet-friendly attractions in Windsor. The Windsor Sculpture Park is dog-friendly, and you can often spot dogs enjoying the trails at the Ojibway Nature Centre.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy than hotels. They're also often located in residential areas, giving you a more authentic experience of the city. And if you're travelling with a family or group, vacation rentals can be a more cost-effective option.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    Windsor is home to the WFCU Centre, a multi-purpose arena that hosts a variety of sporting events, including ice hockey and basketball. The city also has several public parks with sports fields, tennis courts, and swimming pools.

Destinations nearby

Top Holiday Rentals with a Balcony in Windsor

Private balconies with city skyline views come as standard at these holiday rentals in Windsor for a lovely start to your day.

The Bachelor Suite At Stanley/kitchenette&backyard - Windsor
Windsor
28/06 – 31/07
£73/nighttotal: £2409 (33 )

The Bachelor Suite At Stanley/kitchenette&backyard

1 2
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.
Modern & Stylish 4br Home - Near Detroit Downtown - Sleeps 10 - Pet-friendly - Windsor
10 4 reviews
Windsor
16/11 – 07/12
£352/nighttotal: £7392 (21 )

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

4 4
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.
Detroit Mansion | Fireplace Suites | Sleeps 14 - Windsor
Windsor
15/12 – 28/12
£299/nighttotal: £3887 (13 )

Detroit Mansion | Fireplace Suites | Sleeps 14

7 4
apartment , Detroit
This six-bedroom Detroit residence is situated on the East Side, offering a 15-minute drive to Downtown Detroit and a 10-minute drive to Belle Isle Park, with the riverfront accessible within a 700-metre walk or a 4-minute drive.
This spacious flat accommodates up to 14 guests with a fully equipped kitchen, a private garden featuring a barbecue, and a dedicated workspace, making it ideal for families or groups seeking a comfortable stay with convenient access to local attractions.
7br House 19 Ppl Dt Windsor Wd Free Parking - Windsor
10 2 reviews
Windsor
30/06 – 02/07
£441/nighttotal: £882 (2 )

7br House 19 Ppl Dt Windsor Wd Free Parking

7 6
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.

Best Windsor holiday rentals with air conditioning

Modern 3-bed, 2-bath In South Windsor - Windsor
Windsor
25/07 – 31/10
£77/nighttotal: £7546 (98 )

Modern 3-bed, 2-bath In South Windsor

3 1
apartment , Windsor
This three-bedroom, two-bathroom flat is located in the Remington Park district of South Windsor, offering convenient access to St. Clair College (approximately 1.6 kilometres away), the University of Windsor (approximately 3.4 kilometres away), and Devonshire Mall (approximately 1.2 kilometres away).
This property provides parking, air conditioning, and a fully equipped kitchen including a microwave oven and dishwasher, with a peaceful backyard retreat and patio ideal for up to six guests.
Charming Renovated One Bedroom Apartment. - Windsor
9.8 6 reviews
Windsor
13/07 – 17/08
£46/nighttotal: £1610 (35 )

Charming Renovated One Bedroom Apartment.

1 2
apartment , Windsor
This one-bedroom Windsor apartment, situated in South Central Windsor, is conveniently located 1.6km from Jackson Park and 2.1km from the Detroit-Windsor Tunnel, offering easy access to local attractions.
The self-contained flat sleeps three, features a fully equipped kitchen with appliances including a washing machine, free Wi-Fi, a private patio, and is within 2km of Adventure Bay Family Water Park and the Art Gallery of Windsor, making it ideal for exploring the city.
Chagga- 1br Clean-quiet Aptmt-location-rain Shower - Windsor
8.8 59 reviews
Windsor
01/07 – 16/07
£35/nighttotal: £525 (15 )

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.
2 Bed 2 Bath In Downtown Windsor W/ Free Parking - Windsor
9.5 204 reviews
Windsor
10/07 – 11/07
£130/nightfor 1 night

2 Bed 2 Bath In Downtown Windsor W/ Free Parking

1 2
apartment , Windsor
This two-bedroom, two-bathroom duplex is situated in downtown Windsor, a short distance (approximately 1.8km) from Caesars Windsor and within walking distance (0.8km) of the Windsor Aquatic Centre.
The 70-inch TV, Netflix access, keyless entry, and fully equipped eat-in kitchen with granite countertops are among the amenities offered in this self-catering property; it sleeps five guests comfortably.
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