Windsor holiday rentals

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Best Windsor holiday rentals

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£14 - £124£124 - £234£234 - £343£343 - £452£452+ per night

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ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Windsor

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Albert Housing - Windsor - Building
Albert Housing
Windsor, ON, Canada
6.6Okay(64)
Parking
Free Wi-Fi
Air conditioning
£35+
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Affordable Downtown Private Rooms - Windsor - Living room
Affordable Downtown Private Rooms
Windsor, ON, Canada
6.8Okay(3)
Parking
Free Wi-Fi
Air conditioning
£46+
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Beautiful newly designed Luxurious Apartment - Windsor - Bedroom
Beautiful newly designed Luxurious Apartment
Windsor, ON, Canada
8.3Very Good(7)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£110+
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Jnice Residence - Windsor - Building
Jnice Residence
Windsor, ON, Canada
9.6Wonderful(18)
Parking
Free Wi-Fi
Air conditioning
£83+
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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
Free Wi-Fi
Air conditioning
£67+
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Charming Renovated One Bedroom Apartment. - Windsor - Building
Charming Renovated One Bedroom Apartment.
Windsor, ON, Canada
9.6Wonderful(5)
Free Wi-Fi
Air conditioning
£54+
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Private Room in Luxury Penthouse Located in Windsor Lasalle ON - Windsor - Bedroom
Private Room in Luxury Penthouse Located in Windsor Lasalle ON
Windsor, ON, Canada
9.5Wonderful(2)
Parking
Free Wi-Fi
Air conditioning
£55+
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Adorable two bedrooms unit with sperate entrance close to everywhere - Windsor - Kitchen
Adorable two bedrooms unit with sperate entrance close to everywhere
Windsor, ON, Canada
Air conditioning
£53+
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Waterfront Home Windsor ,Canada - Windsor
Waterfront Home Windsor ,Canada
Windsor, ON, Canada
7.8Good(141)
Parking
Free Wi-Fi
Air conditioning
£59+
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5 Bedrooms Modern Oasis In Downtown Area - Windsor
5 Bedrooms Modern Oasis In Downtown Area
City Centre
9.0Wonderful(32)
Parking
Free Wi-Fi
Air conditioning
£57+
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Perfect Location! Quiet-Spacious-2 Bed-2 Bath - Windsor
Perfect Location! Quiet-Spacious-2 Bed-2 Bath
City Centre
8.9Very Good(10)
Free Wi-Fi
Pet-friendly
Air conditioning
£97+
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The Boho Oasis - Windsor
The Boho Oasis
Windsor, ON, Canada
9.8Wonderful(56)
Parking
Free Wi-Fi
Air conditioning
£110+
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Modern & Private 1-Bedroom Apartment - Windsor
Modern & Private 1-Bedroom Apartment
Windsor, ON, Canada
9.3Wonderful(3)
Parking
Air conditioning
£92+
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Stylish 2-Bedroom Apartment In Downtown Windsor - Windsor
Stylish 2-Bedroom Apartment In Downtown Windsor
City Centre
9.0Wonderful(17)
Parking
Free Wi-Fi
Air conditioning
£81+
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Cozy 2 Beds Basement Suite - Windsor
Cozy 2 Beds Basement Suite
Windsor, ON, Canada
8.5Very Good(6)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£51+
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3 bedroom with laundry and parking at Windsor - Windsor
3 bedroom with laundry and parking at Windsor
City Centre
8.4Very Good(10)
Parking
Free Wi-Fi
£167+
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Booking Insights

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.

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

Wednesday offers the lowest rates in Windsor, with an average nightly price of £39. The highest prices are found on Thursday, with average rates at £85.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

August
June
£51
£66
Cheapest month to stay with an average 28% drop in price.
Most expensive month to stay with an average 19% 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 holiday rental deals

  • Pool is the most popular holiday rental property amenity in Windsor
  • Holiday rentals in Windsor are around 238% cheaper 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, 56 reviews), 5 Bedrooms Modern Oasis In Downtown Area (9.0, 32), and 2 Bedroom With Laundry And Parking In Wi (8.9, 24), based on ratings and reviews from real travellers.
  • If you’re looking for a cheap holiday rental in Windsor, you should consider visiting during the low season. The cheapest holiday homes in Windsor can be found in August and October.
  • 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 8 days.

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 holiday rental.

Everything you need to know for your stay in Windsor

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