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The 10 Best Holiday Rentals in Windsor, Canada

Check out our pick of great holiday rentals in Windsor

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Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

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This adult-only bed and breakfast in Windsor, Ontario features a spa bath. Each room includes cable TV and free Wi-Fi and this property is 4 kilometers from Caesars Windsor Casino.

Breakfast is available at the Ye Olde Walkerville Bed & Breakfast. Guests will start their meal with fruit, followed by a choice of light, vegan, sweet or hearty dishes.

The house is in Walkerville, a beautiful area. The room was comfortable, quiet, without the noisy heaters. The breakfast is something really special, the food and the atmosphere is verry familiar.

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9.2
Superb
168 reviews
Price from
£78
per night

Offering a terrace and quiet street view, Windsor Airport Accommodation is situated in Windsor, 11 km from TCF Center and 10 km from GM World. The property is set 10 km from Saint Andrews Hall, 11 km from Music Hall Center and 11 km from Gem Theatre. The apartment features rooms with air conditioning, free private parking and free WiFi.

The accommodations were very clean. Complimentary coffee and tea.

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9.4
Superb
20 reviews
Price from
£47
per night

A recently renovated apartment set in Windsor, The Boho Oasis features a garden. This apartment offers free private parking, a 24-hour front desk and free WiFi. The property offers allergy-free units and is situated 8 km from TCF Center.

Quiet neighborhood, modern and stylish decor, accommodating host, affordable price !

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9.6
Exceptional
26 reviews
Price from
£102
per night

Offering a garden and garden view, A Hidden Gem Bed and Breakfast is situated in Windsor, 4.5 km from TCF Center and 3.8 km from GM World. There is a private entrance at the bed and breakfast for the convenience of those who stay. There is a sun terrace and guests can make use of free WiFi and free private parking.

This was our second stay at A Hidden Gem and we stayed in "the Loft" room. The room is both spacious and cozy at the same time, and has several little "nooks and crannies" throughout the space to cozy up and relax as well as a jacuzzi tub in the bathroom. We are so glad we had some extra time to enjoy sitting in the bay window to read, and take a soak in the tub. The hosts, Sue and Troy, are spectacularly pleasant, and can point you to good restaurants and shops, all within short walking distance from the B&B. The breakfast was amazing - vegetarian quiche, fruit smoothie and delicious carrot/cranberry muffins (among a list of other great options).

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9.9
Exceptional
43 reviews
Price from
£78
per night

Boasting a shared lounge and views of river, WaterfrontHome-RiverView, Windsor, Canada is a homestay set in a historic building in Windsor, 4.5 km from TCF Center. Among the facilities at this property are a shared kitchen and luggage storage space, along with free WiFi throughout the property. The accommodation features private check-in and check-out and bicycle parking for guests.

The property was a very reasonable walk from the train station and fr the avenue pf shops an

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8
Very good
178 reviews
Price from
£49
per night

Equipped with a movie room and game room, this property is located on the campus of St. Clair College. Outdoor BBQ facilities are offered. The property is 9 km from the shopping and dining of downtown Windsor.

Beautiful and serene. My grandson was very impressed and may be a future student?!?!?

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8.1
Very good
258 reviews
Price from
£79
per night

The spacious holiday home features 4 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a bath. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. For added privacy, the accommodation features a private entrance.

Beautiful home and very attentive hosts

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8.7
Fabulous
10 reviews
Price from
£214
per night

Situated in Windsor, 5.1 km from TCF Center, Self contained 2 level apartment with 4 bdrms & 2 bathroom features accommodation with free WiFi and free private parking. The property is located 4.3 km from GM World, 4.7 km from Saint Andrews Hall and 5.1 km from Music Hall Center. The apartment has family rooms.

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10
Exceptional
2 reviews

Situated in Windsor, 5.5 km from GM World, Albert Housing offers accommodation with a hot tub. The air-conditioned accommodation is 6.2 km from TCF Center, and guests can benefit from complimentary WiFi and private parking available on site. Gem Theatre is 6.4 km away and The Fillmore Detroit is 7 km from the homestay.

Very convenient location close to the train station. It was great to be able to rest my head for the night after a long train ride, instead of riding infrequent buses and walking for kilometers and kilometers bc it's Windsor. Nice to find a clean, safe, reasonably priced place.

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7.2
Good
71 reviews
Price from
£46
per night

Set in Windsor and only 18 km from TCF Center, Mulberry court offers accommodation with garden views, free WiFi and free private parking. Guests staying at this apartment have access to a fully equipped kitchenette. The property is non-smoking and is situated 17 km from GM World.

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1
Review score
1 reviews
Price from
£49
per night

Most booked holiday rentals in Windsor this month

Enjoy breakfast in Windsor!

  • Ye Olde Walkerville Bed & Breakfast
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 168 reviews

    This adult-only bed and breakfast in Windsor, Ontario features a spa bath. Each room includes cable TV and free Wi-Fi and this property is 4 kilometers from Caesars Windsor Casino.

    The breakfast was fantastic. I xidn't leave the table hungry.

  • Windsor Airport Accommodation
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 20 reviews

    Offering a terrace and quiet street view, Windsor Airport Accommodation is situated in Windsor, 11 km from TCF Center and 10 km from GM World.

    It was comfortable and the owners were really friendly.

  • The Boho Oasis
    Breakfast options
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 26 reviews

    A recently renovated apartment set in Windsor, The Boho Oasis features a garden. This apartment offers free private parking, a 24-hour front desk and free WiFi.

    Clean and comfortable - well laid out - great value

  • A Hidden Gem Bed and Breakfast
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 43 reviews

    Offering a garden and garden view, A Hidden Gem Bed and Breakfast is situated in Windsor, 4.5 km from TCF Center and 3.8 km from GM World.

    Loved the location, and the host's were super nice.

  • Hotel/Home
    Breakfast options
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 10 reviews

    Featuring air-conditioned accommodation with a balcony, Hotel/Home is located in Windsor. This property offers access to a terrace, free private parking and free WiFi.

  • Self contained 2 level apartment with 4 bdrms & 2 bathroom
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Situated in Windsor, 5.1 km from TCF Center, Self contained 2 level apartment with 4 bdrms & 2 bathroom features accommodation with free WiFi and free private parking.

  • Modern & Private 1-Bedroom Apartment
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    Set in Windsor, 4.4 km from Saint Andrews Hall and 4.8 km from Music Hall Center, Modern & Private 1-Bedroom Apartment offers air conditioning.

These holiday rentals in Windsor have options with FREE cancellation

  • WaterfrontHome-RiverView, Windsor ,Canada
    Free cancellation options available
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 178 reviews

    Boasting a shared lounge and views of river, WaterfrontHome-RiverView, Windsor, Canada is a homestay set in a historic building in Windsor, 4.5 km from TCF Center.

    Didn't have breakfast. Location was easy to find.

  • Residence & Conference Centre - Windsor
    Free cancellation options available
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 258 reviews

    Equipped with a movie room and game room, this property is located on the campus of St. Clair College. Outdoor BBQ facilities are offered.

    Location was ideal. The staff were very friendly.

  • Albert Housing
    Free cancellation options available
    7.2
    Scored 7.2
    Good
    Rated good
     · 71 reviews

    Situated in Windsor, 5.5 km from GM World, Albert Housing offers accommodation with a hot tub.

    It's old but clean. It's good enough for the rate.

  • Mulberry court
    Free cancellation options available
    1.0
    Scored 1.0
    Very poor
    Rated very poor
     · 1 review

    Set in Windsor and only 18 km from TCF Center, Mulberry court offers accommodation with garden views, free WiFi and free private parking.

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