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Windsor vacation rentals

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Booking Insights
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Best Windsor vacation rentals

These are the best prices for Oct 7 - 8.
Windsor Manor - Windsor - Living room
Windsor Manor
City Centre
9.5Wonderful(10)
Apartment
$189+
Check availability
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor. - Windsor - Living room
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
Windsor, ON, Canada
10Wonderful(12)
House
$177+
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Stylish luxury apartment - Windsor - Bedroom
Stylish luxury apartment
Windsor, ON, Canada
8.9Very good(7)
Apartment
$126+
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Executive Home in Windsor close to the airport - Windsor
Executive Home in Windsor close to the airport
Windsor, ON, Canada
9.2Wonderful(14)
House
$136+
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Full house - 5 bed, 2 bath - Windsor - Living room
Full house - 5 bed, 2 bath
Windsor, ON, Canada
9.1Wonderful(22)
House
$192+
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Charming 3-bedroom apartment with AC, WiFi in pleasant Lasalle - Windsor - Living room
Charming 3-bedroom apartment with AC, WiFi in pleasant Lasalle
Windsor, ON, Canada
9.0Wonderful(6)
Apartment
$194+
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Comfy dream • 2 beds • Netflix • fast wifi - Windsor - Kitchen
Comfy dream • 2 beds • Netflix • fast wifi
Windsor, ON, Canada
10Wonderful(2)
House
$192+
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Paradise Home - Your Home Away From Home - Windsor - Patio
Paradise Home - Your Home Away From Home
Windsor, ON, Canada
9.2Wonderful(25)
House
$117+
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Private Hot Tub Retreat, Walk to Caesars, Waterfront & Downtown! - Windsor - Outdoors view
Private Hot Tub Retreat, Walk to Caesars, Waterfront & Downtown!
Windsor, ON, Canada
8.6Very good(15)
House
$234+
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Navy gold dream - 2 bedroom house w/ work station - Windsor - Bedroom
Navy gold dream - 2 bedroom house w/ work station
Windsor, ON, Canada
10Wonderful(1)
House
$196+
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5 Bedrooms Modern Oasis In Downtown Area - Windsor
5 Bedrooms Modern Oasis In Downtown Area
City Centre
7.9Good(53)
Homestay
$69+
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Perfect Location! Quiet-Spacious-2 Bed-2 Bath - Windsor
Perfect Location! Quiet-Spacious-2 Bed-2 Bath
City Centre
8.7Very good(31)
Apartment
$152+
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Downtown-Jackson Park Private Budget Fri - Windsor
Downtown-Jackson Park Private Budget Fri
Windsor, ON, Canada
8.9Very good(5)
Homestay
$47+
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The Boho Oasis - Windsor
The Boho Oasis
Windsor, ON, Canada
9.7Wonderful(67)
Apartment
$143+
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Stylish 2-Bedroom Apartment In Downtown Windsor - Windsor
Stylish 2-Bedroom Apartment In Downtown Windsor
City Centre
7.3Good(24)
Apartment
$107+
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Globalstay. Unique New Townhomes for 16 Guests. Hot Tub, Bbq - Windsor
Globalstay. Unique New Townhomes for 16 Guests. Hot Tub, Bbq
Windsor, ON, Canada
9.0Wonderful(6)
Apartment
$210+
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.

Which month has the cheapest vacation rental rates in Windsor?

Vacation rentals are cheapest in Windsor in July, with average rates of $34. In comparison, March is the most expensive month, with prices at $199.

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

Sunday offers the lowest rates in Windsor, with an average nightly price of $49. The highest prices are found on Friday, with average rates at $166.

How much is a vacation rental in Windsor for tonight by property type?

The best deal for a vacation rental in Windsor found by KAYAK users in the last 5 days was $53 in a Homestay. House prices start at $98.

How much is a vacation rental in Windsor for this weekend by property type?

The best deal for a vacation rental in Windsor found by KAYAK users for the upcoming weekend was $42 in a Apartment. Homestays prices start at $53 and Houses at $223.

How early should you book a vacation rental in Windsor?

Book at least 22 days before your stay begins to get the best price for your Windsor vacation rental.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
July
$69
$160
Cheapest month to stay with an average 38% drop in price.
Most expensive month to stay with an average 65% 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 198% cheaper than hotels on average. Search here to compare prices for all accommodation types in Windsor.
  • The best vacation rental properties in Windsor are Beautifully renovated home in historic Walkerville. (10.0, 21 reviews), The Boho Oasis (9.7, 67), and Paradise Home - Your Home Away From Home (9.2, 25), 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 November and October.
  • The cheapest night for renting a vacation home in Windsor is Sunday. 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 37 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 $543.

  • 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 $2,327.

  • 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, cottages, houses, homestays, studios and villas.

  • 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 Housing Albert.

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

    There are a number of dog and pet-friendly Windsor vacation rentals, with around 12% 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 $53. Search here for similar prices

  • How much is a vacation rental in Windsor for this weekend?

    In the last 72 hours, users have found Windsor vacation rentals for this weekend for as low as $42 per night. 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.

More options for your stay in Windsor