Windsor vacation rentals

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Booking Insights
Recommended by KAYAK

Best Windsor vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$19 - $247$247 - $474$474 - $702$702 - $929$929+ per night

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ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Windsor

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Affordable Downtown Private Rooms - Windsor - Living room
Affordable Downtown Private Rooms
Windsor, ON, Canada
6.8Okay(3)
House
Parking
Free Wi-Fi
$62+
Check availability
Beautiful newly designed Luxurious Apartment - Windsor - Living room
Beautiful newly designed Luxurious Apartment
Windsor, ON, Canada
8.2Very good(8)
Apartment
Parking
Free Wi-Fi
Pet friendly
$137+
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Cheerful Family Home 3 mins drive to UWindsor - Windsor - Living room
Cheerful Family Home 3 mins drive to UWindsor
Windsor, ON, Canada
9.7Wonderful(4)
House
$250+
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Centrally Located 1 Bedroom Apartment with Historical Charm! - Windsor - Building
Centrally Located 1 Bedroom Apartment with Historical Charm!
Windsor, ON, Canada
Apartment
Free Wi-Fi
$87+
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480# Two-bedroom apartment near the border tunnel - Windsor - Kitchen
480# Two-bedroom apartment near the border tunnel
City Centre
8.0Very good(7)
Apartment
Free Wi-Fi
$86+
Check availability
Charming Renovated One Bedroom Apartment. - Windsor - Living room
Charming Renovated One Bedroom Apartment.
Windsor, ON, Canada
9.6Wonderful(5)
Apartment
Free Wi-Fi
$81+
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Waterfront Home Windsor ,Canada - Windsor
Waterfront Home Windsor ,Canada
Windsor, ON, Canada
7.7Good(145)
Homestay
Parking
Free Wi-Fi
$77+
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5 Bedrooms Modern Oasis In Downtown Area - Windsor
5 Bedrooms Modern Oasis In Downtown Area
City Centre
8.7Very good(39)
Homestay
Parking
Free Wi-Fi
$75+
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Windsor Airport Room Accommodation - Windsor
Windsor Airport Room Accommodation
Windsor, ON, Canada
7.3Good(20)
Apartment
Parking
Free Wi-Fi
$119+
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Perfect Location! Quiet-Spacious-2 Bed-2 Bath - Windsor
Perfect Location! Quiet-Spacious-2 Bed-2 Bath
City Centre
9.1Wonderful(13)
Apartment
Free Wi-Fi
Pet friendly
$116+
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The Boho Oasis - Windsor
The Boho Oasis
Windsor, ON, Canada
9.8Wonderful(56)
Apartment
Parking
Free Wi-Fi
$146+
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Stylish 2-Bedroom Apartment In Downtown Windsor - Windsor
Stylish 2-Bedroom Apartment In Downtown Windsor
City Centre
9.1Wonderful(19)
Apartment
Parking
Free Wi-Fi
$107+
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Cozy 2 Beds Basement Suite - Windsor
Cozy 2 Beds Basement Suite
Windsor, ON, Canada
8.3Very good(8)
Apartment
Parking
Free Wi-Fi
Pet friendly
$60+
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Modern & Private 1-Bedroom Apartment - Windsor
Modern & Private 1-Bedroom Apartment
Windsor, ON, Canada
9.3Wonderful(3)
Apartment
Parking
$140+
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3 bedroom with laundry and parking at Windsor - Windsor
3 bedroom with laundry and parking at Windsor
City Centre
8.5Very good(10)
Apartment
Parking
Free Wi-Fi
$219+
Check availability
Great Location -Mural, Barn and Corridor -1 Bed 1Bath Apartments! - Windsor
Great Location -Mural, Barn and Corridor -1 Bed 1Bath Apartments!
City Centre
8.0Very good(4)
Apartment
Parking
Free Wi-Fi
Pet friendly
$86+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Windsor

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Windsor with confidence.

What is the cheapest day of the week to book a vacation rental in Windsor?

Monday offers the lowest rates in Windsor, with an average nightly price of $50. The highest prices are found on Thursday, with average rates at $151.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
December
$75
$90
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 114% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Windsor vacation rental deals

  • Pool is the most popular vacation rental property amenity in Windsor
  • Vacation rentals in Windsor are around 30% cheaper than hotels on average. Search here to compare prices for all accommodation types in Windsor.
  • The best vacation rental properties in Windsor are The Boho Oasis (9.8, 56 reviews), 5 Bedrooms Modern Oasis In Downtown Area (8.7, 39), and Waterfront Home Windsor ,Canada (7.7, 145), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Windsor, you should consider visiting during the low season. The cheapest vacation homes in Windsor can be found in July and January.
  • The cheapest night for renting a vacation home in Windsor is Saturday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windsor for 20 days.

FAQs when booking a vacation home in Windsor

  • How much is a vacation rental for a week in Windsor?

    The average price for a weekly Windsor vacation rental found by KAYAK users in the last 2 weeks is $341.

  • How much is a vacation rental for a month in Windsor?

    The average price for a monthly Windsor vacation rental found by KAYAK users in the last 2 weeks is $1,461.

  • What types of vacation rentals are available in Windsor?

    There are loads of different property types that you can make your vacation home in Windsor. You’ll find apartments, condos, houses and homestays.

  • What are some of the most-loved vacation rentals available in Windsor?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Albert Housing.

  • Are there any pet-friendly vacation rentals in Windsor?

    There are a number of dog and pet-friendly Windsor vacation rentals, with around 9% allowing you to bring your pet along with you.

  • How much is a vacation rental in Windsor for tonight?

    In the last 72 hours, users have found Windsor vacation rentals for tonight for as low as $62. Search here for similar prices

  • How can I find vacation rentals near me in Windsor?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Windsor?

Our map will help you find the perfect place to stay in Windsor by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Windsor