Winchester holiday rentals

We found 4 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Winchester

Are you hoping to discover top things to see and do while you're in town? Venture out of your holiday home and check out everything that makes Winchester a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Morgan County Fairgrounds (12.7 mi / 20.5 km)
  • Old Orchard Country Club (16.7 mi / 26.9 km)

Exploring the natural features in Winchester

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Winchester is a great spot to appreciate mother nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Jacksonville (13.1 mi / 21.1 km)
  • Jacksonville Community Park (13.5 mi / 21.7 km)
  • King Park (18.7 mi / 30.1 km)

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?
The average price for a holiday home in Winchester depends on a number of factors, like season, length of stay and property type. Whether you’re looking for a sprawling house with room for friends and family or an apartment for just you and your sweetheart, just enter your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Winchester?
The average price for a holiday home close to the beach in Winchester depends on when you’re travelling and the type and size of property you’re looking for. Find prices easily and quickly on Stayz by entering your travel dates and destination. Then use the filters to pick the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
How old do you have to be to rent a holiday home in Winchester?
You’ll have to check with the Winchester holiday home you’re looking at on Stayz as the minimum age differs. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
The amount of time you can book a Winchester holiday home for depends on each property. Simply put in your travel dates to browse available options offering longer term stays. They come with all the things you need to make your extended getaway more convenient and comfortable, such as kitchens and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.