Compare Vacation Rentals & Airbnb in Windsor

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Windsor vacation rentals
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1448 Rentals and Airbnb in Windsor

Best family friendly Windsor vacation rentals

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

Corktown Oasis - 4 Br Luxe Getaway Close To Downtown - Windsor
9.8 21 reviews
Windsor
27/06 – 28/06
$1009/nightfor 1 night

Corktown Oasis - 4 Br Luxe Getaway Close To Downtown

4 2
apartment , Detroit
This four-bedroom, one-bathroom townhome offers accommodation in Corktown, Detroit's oldest neighbourhood, located 1.6 kilometres from downtown and within easy reach of Ford Field and Little Caesars Arena.
The 186 square metre property accommodates up to 11 guests with four bedrooms, a pull-out sofa, a fully equipped kitchen featuring a Breville Barista Touch Espresso Machine, a comfortable living room with a 65-inch television, and a dining room with an eight-person table, complemented by a one-car garage and free street parking.
Spacious Detroit Retreat • Sleeps 16 • Parking - Windsor
9.7 107 reviews
Windsor
02/08 – 05/08
$717/nighttotal: $2151 (3 )

Spacious Detroit Retreat • Sleeps 16 • Parking

1 6
apartment , Detroit
This Detroit house, situated in a historic neighbourhood offering easy access to various city landmarks, provides a central location for exploring the Motor City.
Sleeping up to 16 guests in six bedrooms and three bathrooms, this fully renovated property boasts a fully equipped kitchen, PS5, Ms. Pacman arcade game, Tempur-Pedic mattresses, and business-grade Wi-Fi, ideal for large families or groups.
Jp's Dream House - Windsor
9.9 66 reviews
Windsor
02/08 – 05/08
$461/nighttotal: $1383 (3 )

Jp's Dream House

1 6
apartment , Windsor
JP's Dreamhouse, a four-bedroom Windsor property, is centrally located in Windsor, Ontario, offering easy access to various restaurants and shops.
This 10-12 guest dwelling boasts uniquely themed bedrooms, two bathrooms, a garden, parking, and all modern conveniences including air conditioning and internet access, perfect for large groups celebrating special occasions.
Granite Counters, Modern 1br Walk To Casino - Windsor
9.9 88 reviews
Windsor
07/08 – 09/08
$210/nighttotal: $420 (2 )

Granite Counters, Modern 1br Walk To Casino

1 2
apartment , Windsor
Casa Rio 2 is a downtown Windsor flat, a short walk from the Art Gallery of Windsor, Caesars Windsor, and the Detroit-Windsor Tunnel bus stop, providing easy access to Detroit attractions.
This one-bedroom apartment sleeps three, features a fully equipped kitchen, laundry facilities, fast Wi-Fi, and a side porch with stunning Detroit River and city skyline views, including views of Detroit fireworks.

Best Windsor vacation rentals with parking

Modern Boutique Condo - "Au Coeur De Detroit" - Windsor
10 9 reviews
Windsor
04/07 – 05/07
$530/nightfor 1 night

Modern Boutique Condo - "Au Coeur De Detroit"

1 2
apartment , Detroit
This Brush Park flat is located just off Woodward Avenue, offering convenient walking access to major Detroit entertainment venues such as Little Caesars Arena (4 minutes) and Comerica Park (9 minutes), with the Masonic Temple (10 minutes) and Ford Field (14 minutes) also within easy reach.
This 78 square metre condominium accommodates up to four guests, featuring a microwave oven, dishwasher, air conditioning, and a garden, with parking provided and an 11:00 AM check-out time.
Mexicantown Detroit 2br | Sleeps 7 + Wifi - Windsor
Windsor
17/07 – 19/07
$428/nighttotal: $856 (2 )

Mexicantown Detroit 2br | Sleeps 7 + Wifi

3 5
apartment , Detroit
This flat is located in Mexicantown, Detroit, offering convenient access to the TCF Centre, which is 4.8 kilometres away, and the Masonic Temple Theatre, 4.2 kilometres distant.
This 74-square-metre flat sleeps up to seven guests across three bedrooms and includes a kitchen with a fridge and microwave, plus free on-site parking and WiFi.
Walk To Caesars Windsor Sleeps 8 Hot Tub 2 Parking - Windsor
10 9 reviews
Windsor
22/06 – 23/06
$182/nightfor 1 night

Walk To Caesars Windsor Sleeps 8 Hot Tub 2 Parking

1 2
apartment , Windsor
This stylish downtown Windsor flat offers excellent access to Caesars Casino, the riverfront, and a range of dining and entertainment options, all within a short walk.
This property sleeps up to eight guests and features two bedrooms, one bathroom, air conditioning, a fully equipped kitchen, on-site parking for two vehicles, and an optional private hot tub spa for an additional fee.
The Bachelor Suite At Stanley/kitchenette&backyard - Windsor
Windsor
28/06 – 31/07
$136/nighttotal: $4488 (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.

Frequently Asked Questions about vacation rentals in Windsor

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

    Windsor is a charming city with a rich history and vibrant culture. A first-time visitor should definitely check out the historic Fort Malden, stroll along the beautiful waterfront, and explore the art scene at the Art Gallery of Windsor. You'll also want to take a trip across the Detroit River to the USA and experience the unique atmosphere of Detroit.
  • What are the best Airbnb and vacation rentals in Windsor?

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

    The Old Walkerville area is a popular choice for a vacation rental, it's got lots of historic buildings and is close to the riverfront. The Sandwich neighbourhood is also a good option, it's a bit quieter but still close to all the action.
  • What are the most popular Airbnbs in Windsor?

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

    The Windsor International Aquatic Centre is a great place for kids to splash around, and the Ojibway Nature Centre is a great place to learn about the local wildlife. The Windsor Sculpture Park is also a good option, there's plenty of space for kids to run around.
  • What are the best vacation 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 in the spring or autumn, when the weather is mild and there are fewer tourists. If you're looking for a bargain, you can often find good deals in the winter, but be prepared for cold 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?

    Windsor hosts a variety of events and festivals throughout the year. The Windsor International Film Festival is a popular event in the fall, while the Windsor Jazz Festival takes place in the summer. The annual Windsor International Wine Festival is another highlight, offering tastings from local and international wineries.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

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

    The Windsor Sculpture Park is a great free activity, and the Ojibway Nature Centre is also free to enter. If you're looking for a cheap bite to eat, there are plenty of food trucks and cafes in the city.
  • What are the best restaurants with local dishes in Windsor, Ontàrio, Canadà?

    For a taste of local cuisine, try The Colosseum, a popular spot for Italian food, or The Old Mill, which serves up classic Canadian fare. If you're looking for something a bit more casual, The Burger Bar is a great option.
  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a great option for a walk or bike ride, it follows the Detroit River and offers stunning views of the city. The Ojibway Park is also a great place to go for a walk or cycle, there are plenty of trails to explore.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    The Ojibway Nature Centre is a great pet-friendly attraction, there are plenty of trails for dogs to explore. The Windsor Sculpture Park is also pet-friendly, just make sure your dog is on a leash.
  • 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're often more affordable. They can also be a good option for families or groups of friends travelling together.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    The WFCU Centre is home to the Windsor Spitfires hockey team and hosts a variety of other sporting events. The University of Windsor is also home to a number of sporting facilities, including a swimming pool and fitness centre.

Destinations nearby

Best Windsor vacation rentals with a balcony

Unique 2-bdr Historic Warehouse Loft With Terrace And Fireplace ! ! ! - Windsor
10 7 reviews
Windsor
25/11 – 30/11
$351/nighttotal: $1755 (5 )

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.
Chacha's Place Retreat - Windsor
9.6 26 reviews
Windsor
01/10 – 31/12
$177/nighttotal: $16107 (91 )

Chacha's Place Retreat

3 2
apartment , Detroit
This Detroit detached house is centrally situated for easy access to major motorways, placing downtown Detroit less than 10 kilometres away and other city attractions within a 15-kilometre commute, with landmarks like the Fox Theatre and Greenfield Village nearby.
This spacious 121 square metre property sleeps seven guests across three bedrooms and features a remodelled kitchen and bathroom, air conditioning, a balcony, garden, parking, and a relaxing outdoor sitting porch.
Modern & Stylish 4br Home - Near Detroit Downtown - Sleeps 10 - Pet-friendly - Windsor
10 4 reviews
Windsor
02/08 – 05/08
$603/nighttotal: $1809 (3 )

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.
Unique 2-bdr Historic Warehouse Loft With Terrace ! ! ! - Windsor
9.7 34 reviews
Windsor
20/07 – 22/07
$303/nighttotal: $606 (2 )

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

2 2
apartment , Windsor
The Warehouse apartment in Windsor offers a spacious two-bedroom flat, conveniently located approximately 2.7km from Saint Andrew's Hall and within a 3.2km radius of other attractions including the Music Hall Centre and the TCF Centre.
This 102 square metre Windsor property sleeps up to nine guests and boasts a terrace with river views, a garden, tennis court, parking, and a well-equipped kitchen; on-site amenities include a children's playground and a casino.

Neighborhoods and points of interest in Windsor

Best Windsor vacation rentals with air conditioning

Cozy 2-br Private Lower Suit - Windsor
9.5 12 reviews
Windsor
25/07 – 26/07
$173/nightfor 1 night

Cozy 2-br Private Lower Suit

2 4
apartment , Windsor
This Windsor basement flat offers convenient access to a nearby shopping mall, Walmart, and the expressway, with bus stops also within easy reach.
The self-contained property sleeps four guests comfortably across two bedrooms (one queen, one twin), featuring a full kitchen with modern appliances, a dedicated office space, two free parking spots, Netflix & Prime, and fresh towels provided.
Unique Downtown Location - Windsor
8.0 3 reviews
Windsor
26/06 – 18/07
$174/nighttotal: $3828 (22 )

Unique Downtown Location

1 4
apartment , Windsor
This 3-bedroom flat for 4 guests is situated in downtown Windsor, a 4-minute walk (approximately 320 metres) from the riverfront and close to Ouellette Street's amenities.
This second-floor loft offers a spacious layout, air conditioning, a kitchen, and internet, with pets allowed, making it ideal for urban exploration and university visits.
Hometown Folks Desirable Riverside/east Windsor - Windsor
9.2 60 reviews
Windsor
17/07 – 19/07
$408/nighttotal: $816 (2 )

Hometown Folks Desirable Riverside/east Windsor

4 2
apartment , Windsor
This house is located in Riverside, just a short distance from the Windsor Family Credit Union Centre and other attractions, offering a peaceful escape from the city centre. The property has received excellent ratings for its cleanliness, location and overall experience.
The house has four bedrooms, providing plenty of space for families or groups of friends. Guests can enjoy a private garden, a terrace, and a fully equipped kitchen, as well as free Wi-Fi, parking and air conditioning.
2 Cozy, Farmers Mrkt, Iptv, Outdoor Patio, Casino - Windsor
10 3 reviews
Windsor
01/07 – 31/07
$87/nighttotal: $2610 (30 )

2 Cozy, Farmers Mrkt, Iptv, Outdoor Patio, Casino

1 2
apartment , Windsor
This one-bedroom flat offers a prime downtown Windsor location, placing you in one of the city's best central spots with convenient self check-in and private access to the entire accommodation.
Guests can enjoy a stylish, cosy one-bedroom flat with a kitchen featuring a fridge, freezer, and microwave, air conditioning, a garden, a sauna, and one bathroom, accommodating up to two people with access to a beautifully decorated outdoor patio.
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