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Travel insights for holiday rentals in Winchester
Use these up-to-date, data-driven insights about booking a holiday rental in Winchester including ideal times to book, pricing trends, and more.
What is the cheapest month to book a vacation rental in Winchester?
The cheapest month to book a vacation rental in Winchester is December ($85). Conversely, the most expensive month to stay in Winchester is June ($316).
What is the cheapest day to stay in a vacation rental in Winchester?
The cheapest day to stay in Winchester is Wednesday ($72). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $171.
Discover affordable stays in Winchester that provide a quality experience without breaking the bank. Hotels in Winchester can be found for as low as $262 per night. There is currently one property in Winchester that can be booked for this price. South Winchester Lodges is one of the hotels that can be booked for the lowest price in Winchester. Price data was last updated on 1 May 2025
For those on a budget, these are the cheapest vacation rentals available in Winchester for the selected dates. Prices will typically fluctuate depending on the dates selected, star rating of vacation rental, and vacation rental location.
Find the perfect holiday rental for your stay in Winchester. There are 243 hotels in Winchester and price data was last updated on 1 May 2025. The average price for a hotel in Winchester is $164/night.
Explore different neighbourhoods and areas within Winchester to find the perfect location for your stay. Map data was last updated on 1 May 2025.
Scroll through the map to find vacation rentals close to the Winchester neighborhood(s) you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular vacation rental.
Facts about staying in Winchester
Find useful tips and insights about staying in Winchester to help you make the most of your experience. FAQs were last updated on 1 May 2025.
How much does a holiday rental in Winchester cost?
The average cost for a holiday rental in Winchester is $165/night. A good holiday rental deal in Winchester would be for $163/night or less. The cheapest rental deal found recently by our users was $34/night. If you’re flexible with your travel dates, then try to avoid booking June, the most expensive month of the year. Booking April is the cheapest month to book a holiday rental in Winchester.
What part of Winchester is best to stay in?
Downtown is the best part of Winchester to stay in based on our user data. Out of all our users who looked at Winchester holiday rentals, 97% of them looked for stays in the Downtown neighbourhood in the last year. The Two Bare Feet happens to be the most popular holiday rental in the Downtown neighbourhood of Winchester.
Are there any Bed & Breakfast holiday rentals in Winchester?
Yes, there are 14 Bed & Breakfast holiday rentals in Winchester. According to our data, Otters Green is currently the most popular Bed & Breakfast rental in the city.
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