Holiday Rentals in Windsor

1448 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Windsor holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

Boutique 1-bedroom Condo In Heart Of Motor City - Windsor
10 12 reviews
Windsor
22/06 – 24/06
£219/nighttotal: £438 (2 )

Boutique 1-bedroom Condo In Heart Of Motor City

1 2
apartment , Detroit
This Brush Park condo in Detroit offers convenient access to major sports venues and public transportation, with Little Caesars Arena and Comerica Park a short walk away.
This apartment provides a 1-bedroom, 1-bathroom unit for up to 4 guests, featuring air conditioning, Wi-Fi, a fully equipped kitchen, and on-site laundry facilities, all within easy reach of the Fox Theatre and the Detroit-Windsor Tunnel.
Private 2br Main Floor Suite Near Border Casino Uwin Hospital - Windsor
Windsor
07/10 – 09/10
£64/nighttotal: £128 (2 )

Private 2br Main Floor Suite Near Border Casino Uwin Hospital

2 2
apartment , Windsor
This two-bedroom main floor suite in Windsor offers convenient access to Detroit's GM World (5.1 km), The Fillmore Detroit (6.8 km), and TCF Center (5.8 km), situated close to the border for easy travel between cities.
This air-conditioned flat provides 60 square meters of living space with a kitchen equipped with a fridge and microwave, accommodating up to seven guests with complimentary WiFi and on-site parking.
Executive Condo. 3br, King Bed W/ Ensuite - Windsor
10 2 reviews
Windsor
01/10 – 31/12
£102/nighttotal: £9282 (91 )

Executive Condo. 3br, King Bed W/ Ensuite

3 2
apartment , Windsor
This three-bedroom executive condo is situated in East Windsor, a short distance from attractions such as the Fox Theatre and The Colosseum.
Offering 223 square metres of space, this Windsor apartment sleeps six guests and boasts a fully equipped kitchen, king-sized bed with ensuite, free Wi-Fi, and a spa, plus easy access to Lakeshore Woods and Willistead Park.
70 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Windsor
Windsor
07/07 – 24/08
£171/nighttotal: £8208 (48 )

70 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

1 3
apartment , Detroit
Holiday rental for 4 guests. Your accommodation will be located in Detroit.
Facilities and services: a freeze, a kitchen and a fridge. Take advantage of the Free Parking with this accommodation.

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.

Trendy Home - Historic Walkerville Distillery District - Windsor
10 1 review
Windsor
01/07 – 03/07
£172/nighttotal: £344 (2 )

Trendy Home - Historic Walkerville Distillery District

2 5
apartment , Windsor
This renovated 1890s residence, located in Windsor's historic Walkerville Distillery District, offers proximity to local shops and restaurants, with Windsor train station 700 metres away and easy access to cultural sites such as the Fox Theatre and the Detroit Windsor Tunnel.
This two-bedroom, two-bathroom flat accommodates up to five guests, featuring exposed brick, a modern kitchen with quartz countertops, a spacious garden with a BBQ, and is within driving distance of Detroit's Ford Field and Comerica Park.
Couple's Romantic Retreat With Hot Tub, Fire Pit. - Windsor
9.7 131 reviews
Windsor
20/06 – 27/06
£179/nighttotal: £1253 (7 )

Couple's Romantic Retreat With Hot Tub, Fire Pit.

1 2
apartment , Windsor
This apartment is located in a quiet residential area of Windsor, just a short walk from parks and trails and within easy reach of the town's attractions. It has received excellent ratings for its cleanliness, location, and overall experience.
The self-catering apartment can accommodate two guests and features a well-equipped kitchen, a private backyard with a hot tub, and a luxurious spa shower. Guests can also enjoy a massage table, a private garage, and proximity to local amenities.
Executive Home In Windsor Close To The Airport - Windsor
9.7 46 reviews
Windsor
01/07 – 03/07
£121/nighttotal: £242 (2 )

Executive Home In Windsor Close To The Airport

1 5
house , Windsor
This Windsor house rental is ideally situated a short 5km drive from Windsor Airport, 5km from Devonshire Mall, and a 24km drive from the Canada–US border, offering easy access to Riverside and local beaches.
The two-bedroom, two-bathroom property sleeps five guests and includes a fully equipped gourmet kitchen with high-end appliances, a spacious living area with a smart TV, and en-suite bathrooms with rainfall showers; fast Wi-Fi and a washer/dryer are also provided.
Luxury Unit Windsor (4-plex) 5 Minutes To Ambassador Bridge - Windsor
Windsor
07/07 – 24/08
£109/nighttotal: £5232 (48 )

Luxury Unit Windsor (4-plex) 5 Minutes To Ambassador Bridge

2 3
apartment , Windsor
This South Cameron flat is conveniently located 1.9km from Mic Mac Park, under 5km from the University of Windsor and the Windsor Riverfront.
The two-bedroom, two-bathroom apartment sleeps four, offering a fully equipped kitchen, including a dishwasher, a Smart TV, and on-site parking; nearby attractions include the Ambassador Bridge and Ojibway Prairie Provincial Nature Reserve.

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
01/07 – 31/08
£74/nighttotal: £4514 (61 )

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 & Private 1-bedroom Apartment - Windsor
9.4 75 reviews
Windsor
25/11 – 30/11
£93/nighttotal: £465 (5 )

Modern & Private 1-bedroom Apartment

1 2
apartment , Windsor
This modern flat is situated in Windsor, just 3km from the TCF Center and 2.5km from GM World, offering easy access to the city's attractions. The property has received excellent ratings for cleanliness and user experience, and a very good rating for location.
The flat can accommodate up to 4 guests and features a private entrance, balcony, and a fully equipped kitchen. Guests can enjoy amenities such as free private parking, air conditioning, and access to a garden, making it a comfortable and convenient base for exploring Windsor.
Executive One-bedroom Upper Unit - Windsor
9.0 2 reviews
Windsor
24/07 – 25/07
£144/nightfor 1 night

Executive One-bedroom Upper Unit

2 2
apartment , Windsor
This holiday flat in Tecumseh provides convenient access to local attractions, situated a 4-minute drive from Lake St. Clair and a 5-minute drive from the Windsor Family Credit Union Centre.
This property offers accommodation for up to four guests with two bedrooms and one bathroom, featuring a fully equipped kitchen, air conditioning, complimentary Wi-Fi, a balcony with outdoor furniture, and an in-unit washer and dryer.
A Supreme Stay In Motown Star Florence Ballard's Home - Windsor
Windsor
20/06 – 27/06
£313/nighttotal: £2191 (7 )

A Supreme Stay In Motown Star Florence Ballard's Home

4 8
apartment , Detroit
This historic residence on Buena Vista Street in Detroit, once home to Florence Ballard of The Supremes, offers a meticulously restored 1960s experience and is situated conveniently near attractions such as the Henry Ford Museum (approximately 8 kilometres away) and the Fox Theatre.
This 278 square metre, three-level dwelling accommodates up to 10 guests across four bedrooms and two bathrooms, featuring two kitchens, two living rooms, two formal dining rooms, a 1966 Magnavox console stereo, and three outdoor spaces, with off-street parking available for five vehicles.

Best Windsor holiday rentals with air conditioning

Bright And Cozy Nest In The City 1br Near River, Swim Park, Casino & Tunnel - Windsor
10 11 reviews
Windsor
19/06 – 21/06
£190/nighttotal: £380 (2 )

Bright And Cozy Nest In The City 1br Near River, Swim Park, Casino & Tunnel

1 2
apartment , Windsor
This Windsor City Centre flat is conveniently located less than 1.3km from Windsor Riverfront, Caesars Windsor, and Caesars Casino, and under 1.6km from the Detroit-Windsor Tunnel.
The 42-square-metre self-catering apartment sleeps three guests and boasts a fully equipped kitchen, private terrace, in-unit laundry, and access to a swimming pool and on-site water park.
The Parkside Lofts | Modern Studio With Style - Windsor
9.5 12 reviews
Windsor
01/07 – 31/08
£44/nighttotal: £2684 (61 )

The Parkside Lofts | Modern Studio With Style

1 2
apartment , Windsor
This West Windsor studio apartment is situated a short distance from the University of Windsor and the waterfront, offering easy access to Windsor city centre.
The self-catering unit, sleeping up to two guests, includes a private kitchen with fridge, freezer, and microwave, a bathroom, in-unit laundry, and high-speed Wi-Fi; free parking is available.
Stunning 3 Bedroom Single Family Home. - Windsor
9.4 77 reviews
Windsor
07/10 – 09/10
£138/nighttotal: £276 (2 )

Stunning 3 Bedroom Single Family Home.

3 2
apartment , Windsor
This three-bedroom home is situated along the Little River Corridor in Windsor, just a short drive from the city centre and the Detroit River. It has received excellent ratings for location, cleanliness and user experience.
The property is spacious at 111 square metres and features a fully equipped kitchen, a private deck and a fenced garden. Enjoy modern amenities such as air conditioning, a washer and dryer, and a Samsung Smart TV Plus, as well as the peace of mind provided by a Ring Smart Home Security system.
Renovated | Sleeps 25 | 4 Kitchens | Game Room - Windsor
10 1 review
Windsor
08/08 – 10/08
£1203/nighttotal: £2406 (2 )

Renovated | Sleeps 25 | 4 Kitchens | Game Room

1 15
apartment , Detroit
This large flat is located just 2 minutes from Belle Isle, offering excellent outdoor recreation, and 10 minutes from downtown Detroit's stadiums and casinos.
This renovated property accommodates up to 25 guests across three connected living spaces, boasting seven bedrooms, six bathrooms, four kitchens, and a game room with ping pong, foosball, and shuffleboard.
©2026 cozycozy.com