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, bungalows, chalets, condos, cottages, houses, homestays and villas.

Are there any pet-friendly vacation rentals in Windsor?

There are a number of dog and pet-friendly Windsor vacation rentals, with around 8% 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 C$ 111.

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.

Windsor Vacation Rentals from C$ 153/night

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Best Windsor vacation rentals

King Edward Apartments

Windsor, ENG, United Kingdom

9.2Wonderful(377)

Free Wi-Fi

C$ 434+

Check availability

Urban Living's - Windsor Castle Luxury Apartments

Windsor, ENG, United Kingdom

8.5Very good(100)

Free Wi-Fi

C$ 529+

Check availability

New Stylish 2-Bed Retreat in Central Windsor

Windsor, ENG, United Kingdom

8.2Very good(60)

Parking

Free Wi-Fi

C$ 409+

Check availability

Penthouse Living by Lawsons

Windsor, ENG, United Kingdom

9.1Wonderful(6)

Free Wi-Fi

C$ 339+

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Riverside Boat Retreat on the river Thames

Windsor, ENG, United Kingdom

8.6Very good(9)

Parking

Free Wi-Fi

C$ 300+

Check availability

Contemporary Boutique 4 Sleeper Eton High Street

Windsor, ENG, United Kingdom

8.1Very good(31)

Parking

Free Wi-Fi

C$ 325+

Check availability

Hampden Apartments - The Diana

Windsor, ENG, United Kingdom

8.7Very good(97)

Parking

Free Wi-Fi

C$ 229+

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Stunning Central Windsor Town House With Parking

Windsor, ENG, United Kingdom

9.0Wonderful(63)

Parking

Free Wi-Fi

C$ 681+

Check availability

Comfort Sleep - Rooms with shared facilities

Windsor, ENG, United Kingdom

5.6Fair(62)

Parking

Free Wi-Fi

C$ 111+

Check availability

Windsorian Experience

Windsor, ENG, United Kingdom

Free Wi-Fi

Windsor, ENG, United Kingdom

7.5Good(17)

Parking

Free Wi-Fi

Pet friendly

C$ 164+

Check availability

Heart of Windsor

Windsor, ENG, United Kingdom

9.5Wonderful(155)

Parking

C$ 250+

Check availability

Lay Your Hat Apartments

Windsor, ENG, United Kingdom

9.2Wonderful(16)

Free Wi-Fi

C$ 216+

Check availability

Castle Properties:Eton-The College

Windsor, ENG, United Kingdom

9.3Wonderful(490)

Free Wi-Fi

C$ 540+

Check availability

Lovely 2-Bed In Windsor Free Parking, 1 Mile From Legoland

Windsor, ENG, United Kingdom

8.4Very good(73)

Parking

Free Wi-Fi

C$ 328+

Check availability

The Clockhouse

Windsor, ENG, United Kingdom

9.6Wonderful(200)

Parking

Free Wi-Fi

C$ 256+

Check availability

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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 February, with average rates of C$ 176. In comparison, June is the most expensive month, with prices at C$ 519.

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 C$ 232. The highest prices are found on Sunday, with average rates at C$ 444.

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Parking and pet friendly are the most popular vacation rental property amenities in Windsor
Vacation rentals in Windsor are around 80% cheaper than hotels on average. Search here to compare prices for all accommodation types in Windsor.
The best vacation rental properties in Windsor are Stunning 1Bd with Castle View (9.8, 52 reviews), Willow Court Farm (9.7, 179), and Luxury Cabin near Legoland, Windsor, Ascot and Lapland with enclosed garden (9.7, 117), based on ratings and reviews from real travelers.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windsor for 47 days.

See more tips

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, bungalows, chalets, condos, cottages, houses, homestays and villas.
Are there any pet-friendly vacation rentals in Windsor?
There are a number of dog and pet-friendly Windsor vacation rentals, with around 8% 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 C$ 111. 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.