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Vacation rentals in Windsor

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Travel insights for holiday rentals in Windsor

Use these up-to-date, data-driven insights about booking a holiday 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 Thursday (S$ 143). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 815.

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

Save money by booking a vacation rental at least 31 days before your trip to Windsor. The lowest price found when booking 31 days ahead was S$ 173 per night.
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Other accommodations in Windsor

Find the perfect holiday rental for your stay in Windsor. There are 469 hotels in Windsor and price data was last updated on 13 September 2025. The average price for a hotel in Windsor is .
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
S$ 187
Avg. per night
View Deal
The Royal Adelaide Hotel
The Royal Adelaide Hotel

The Royal Adelaide Hotel

46 Kings Road, Windsor, United Kingdom
0.8 km from city centre
Free Wi-Fi
S$ 186
Avg. per night
View Deal
Holiday Inn Express Windsor By IHG
Holiday Inn Express Windsor By IHG

Holiday Inn Express Windsor By IHG

71 Alma Road, Windsor, United Kingdom
0.5 km from city centre
Free Wi-Fi
S$ 174
Avg. per night
View Deal
Oakley Court
Oakley Court

Oakley Court

Windsor Road, Windsor, United Kingdom
4.1 km from city centre
Pool
Free Wi-Fi
S$ 483
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
S$ 243
Avg. per night
View Deal
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
S$ 249
Avg. per night
View Deal
The Windsor Trooper Pub & Inn
The Windsor Trooper Pub & Inn

The Windsor Trooper Pub & Inn

97 St. Leonard's Road, Windsor, United Kingdom
0.5 km from city centre
Free Wi-Fi
S$ 104
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
S$ 114
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 13 September 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 13 September 2025.

  • How much does a holiday rental in Windsor cost?

    On average, it costs S$ 243 per night for a Windsor holiday rental, but S$ 234 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Windsor was for S$ 61 per night. If you can, try to avoid booking your rental June (as this is the most expensive month). Booking March (the cheapest month) may end up saving you money.

  • Are there any Inn holiday rentals in Windsor?

    There are 5 holiday rentals in Windsor that fall under the Inn category, the most popular is The Union Inn.

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