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Vacation rentals in Windsor

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Travel insights for vacation rentals in Windsor

Use these up-to-date, data-driven insights about booking a vacation rental in Windsor including ideal times to book, pricing trends, and more.

What is the cheapest day to stay in a vacation rental in Windsor?

The cheapest day to stay in Windsor is Wednesday (C$ 165). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 546.

How far ahead should you book a vacation rental in Windsor?

Save money by booking a vacation rental at least 17 days before your trip to Windsor. The lowest price found when booking 17 days ahead was C$ 167 per night.
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Other accommodations in Windsor

Find the perfect vacation rental for your stay in Windsor. There are 374 hotels in Windsor and price data was last updated on 8 December 2025. The average price for a hotel in Windsor is .
The Rutlands B&B
The Rutlands B&B

The Rutlands B&B

102 St Leonards road, Windsor, United Kingdom
0.6 km from city centre
Free Wi-Fi
C$ 253
Avg. per night
View Deal
King Edward Apartments
King Edward Apartments

King Edward Apartments

Windsor, United Kingdom
0.7 km from city centre
Airport shuttle
C$ 225
Avg. per night
View Deal
Legoland Windsor Resort
Legoland Windsor Resort

Legoland Windsor Resort

Winkfield Road, Windsor, United Kingdom
3.1 km from city centre
Pool
Free Wi-Fi
Parking
C$ 158
Avg. per night
View Deal
Charles House - Windsor Castle
Charles House - Windsor Castle

Charles House - Windsor Castle

89 Arthur Road, Windsor, United Kingdom
0.2 km from city centre
Free Wi-Fi
C$ 109
Avg. per night
View Deal
The Windsor Trooper Pub & Inn
The Windsor Trooper Pub & Inn

The Windsor Trooper Pub & Inn

97 St. Leonards Road, Windsor, United Kingdom
0.5 km from city centre
Free Wi-Fi
C$ 88
Avg. per night
View Deal
The Union Inn
The Union Inn

The Union Inn

17 Crimp Hill Road, Windsor, United Kingdom
3.2 km from city centre
Airport shuttle
C$ 122
Avg. per night
View Deal
Toby Carvery Old Windsor by Innkeeper's Collection
Toby Carvery Old Windsor by Innkeeper's Collection

Toby Carvery Old Windsor by Innkeeper's Collection

Straight Road, Windsor, United Kingdom
2.9 km from city centre
Free Wi-Fi
C$ 106
Avg. per night
View Deal
Stable House - Eton Windsor
Stable House - Eton Windsor

Stable House - Eton Windsor

Windsor, United Kingdom
0.8 km from city centre
C$ 453
Avg. per night
View Deal

Where to stay in Windsor

Explore different neighbourhoods and areas within Windsor to find the perfect location for your stay. Map data was last updated on 8 December 2025.
Scroll to and zoom in on the areas in Windsor you plan on visiting to find nearby properties. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

Facts about staying in Windsor

Find useful tips and insights about staying in Windsor to help you make the most of your experience. FAQs were last updated on 8 December 2025.

  • How much does a vacation rental in Windsor cost?

    Windsor vacation rentals are C$ 269/night on average. However, you may find that prices fluctuate depending on the time of year. For example, December is the most expensive month to book a vacation rental in Windsor, and October is often the cheapest month to book. Recently, our users found rentals for C$ 110/night - which is currently the cheapest price. Keep in mind that anything C$ 235/night or less is still considered a good deal.

  • Are there any Inn vacation rentals in Windsor?

    Yes, there are 5 Inn vacation rentals in Windsor. According to our data, Toby Carvery Old Windsor by Innkeeper's Collection is currently the most popular Inn rental in the city.

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