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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 month to book a vacation rental in Windsor?

The cheapest month to book a vacation rental in Windsor is March ($84). Conversely, the most expensive month to stay in Windsor is June ($296).

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

The cheapest day to stay in Windsor is Thursday ($95). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $280.

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 $66 per night.

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Other accommodations in Windsor

Find the perfect holiday rental for your stay in Windsor. There are 373 hotels in Windsor and price data was last updated on 1 February 2026. The average price for a hotel in Windsor is $177/night.
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
$117
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
$115
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
Parking
$326
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
$80
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
$88
Avg. per night
View Deal
Innkeeper's Lodge Old Windsor
Innkeeper's Lodge Old Windsor

Innkeeper's Lodge Old Windsor

Straight Road, Windsor, United Kingdom
2.9 km from city centre
Free Wi-Fi
$80
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
$187
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
$93
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 1 February 2026.
Navigate to the areas in Windsor you plan to visit to find vacation rentals that are close by. 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 1 February 2026.

  • How much does a holiday rental in Windsor cost?

    The average cost for a holiday rental in Windsor is $177/night. A good holiday rental deal in Windsor would be for $153/night or less. The cheapest rental deal found recently by our users was $67/night. If you’re flexible with your travel dates, then try to avoid booking December, the most expensive month of the year. Booking February is the cheapest month to book a holiday rental in Windsor.

  • Are there any Inn holiday rentals in Windsor?

    Yes, there are 5 Inn holiday rentals in Windsor. According to our data, Innkeeper's Lodge Old Windsor is currently the most popular Inn rental in the city.

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