What types of holiday rentals are available in Windsor?

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

Are there any pet-friendly holiday rentals in Windsor?

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

How much is a holiday rental in Windsor for tonight?

In the last 72 hours, users have found Windsor holiday rentals for tonight for as low as £42.

How much is a holiday rental in Windsor for this weekend?

In the last 72 hours, users have found Windsor holiday rentals for this weekend for as low as £115 per night.

How can I find holiday rentals near me in Windsor?

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

Windsor Holiday Rentals from £29/night

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Best Windsor holiday rentals

Albert Housing

Windsor, ON, Canada

6.2Okay(59)

Parking

Free Wi-Fi

Air conditioning

£46+

Check availability

Affordable Downtown Private Rooms

Windsor, ON, Canada

7.0Good(3)

Parking

Free Wi-Fi

Air conditioning

£46+

Check availability

Olde Walkerville Private 1bd/1ba Main Floor Apt.

Windsor, ON, Canada

Free Wi-Fi

Air conditioning

£46+

Check availability

Beautiful newly designed Luxurious Apartment

Windsor, ON, Canada

8.8Very Good(2)

Parking

Free Wi-Fi

Pet-friendly

Air conditioning

£91+

Check availability

2 Bedroom With Laundry And Parking In Wi

City Centre

Air conditioning

Windsor, ON, Canada

Parking

Free Wi-Fi

Air conditioning

Windsor, ON, Canada

Air conditioning

Cheerful Family Home - 3 mins drive to UWindsor

Windsor, ON, Canada

9.7Wonderful(4)

Air conditioning

£242+

Check availability

The Olde Walkerville Loft - 1bd/1ba Apartment

Windsor, ON, Canada

Free Wi-Fi

Pet-friendly

Air conditioning

£48+

Check availability

Charming Renovated One Bedroom Apartment.

Windsor, ON, Canada

Free Wi-Fi

Air conditioning

£58+

Check availability

Centrally Located 1 Bedroom Apartment with Historical Charm!

Windsor, ON, Canada

Free Wi-Fi

Air conditioning

£50+

Check availability

$Executive 2bd 58\' Tv+wifi+ac+parking+kitchen - Windsor - Living room$

Executive 2bd 58\' Tv+wifi+ac+parking+kitchen

Windsor, ON, Canada

Air conditioning

£98+

Check availability

Paradise Home - Your Home Away From Home

Windsor, ON, Canada

Free Wi-Fi

Air conditioning

£116+

Check availability

Waterfront Home Windsor ,Canada

Windsor, ON, Canada

7.6Good(107)

Parking

Free Wi-Fi

Air conditioning

£56+

Check availability

Modern & Private 1-Bedroom Apartment

Windsor, ON, Canada

9.5Wonderful(2)

Parking

Air conditioning

£116+

Check availability

5 Bedrooms Modern Oasis In Downtown Area

City Centre

8.6Very Good(13)

Parking

Free Wi-Fi

Air conditioning

£55+

Check availability

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KAYAK’s insights for holiday 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 September, with average rates of £30. In comparison, March is the most expensive month, with prices at £141.

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 £33. The highest prices are found on Saturday, with average rates at £110.

Find deals

Low season	October
High season	August
Average price (weeknight)	£45
Average price (weekend night)	£56

Cheapest month to stay with an average 9% drop in price.

Most expensive month to stay with an average 28% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

Pet-friendly and pool are the most popular holiday rental property amenities in Windsor
Holiday rentals in Windsor are around 21% more expensive than hotels on average. Search here to compare prices for all accommodation types in Windsor.
The best holiday rental properties in Windsor are The Boho Oasis (9.8, 54 reviews), 2 Bedroom With Laundry And Parking In Wi (8.9, 24), and Windsor Airport Accommodation (7.9, 20), based on ratings and reviews from real travellers.
The cheapest night for renting a holiday home in Windsor is Sunday. In contrast, the most expensive is Saturday.
Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Windsor for 4 days.

See more tips

What types of holiday rentals are available in Windsor?
There are loads of different property types that you can make your holiday home in Windsor. You’ll find apartments, condos, houses, homestays and villas.
Are there any pet-friendly holiday rentals in Windsor?
There are a number of dog and pet-friendly Windsor holiday rentals, with around 9% allowing you to bring your pet along with you.
How much is a holiday rental in Windsor for tonight?
In the last 72 hours, users have found Windsor holiday rentals for tonight for as low as £42. Search here for similar prices
How much is a holiday rental in Windsor for this weekend?
In the last 72 hours, users have found Windsor holiday rentals for this weekend for as low as £115 per night. Search here for similar prices
How can I find holiday rentals near me in Windsor?
Take a look at our holiday rentals map to find the best holiday rental homes near you.