Winchester holiday rentals

We found 1 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 or friends, you'll find the amenities that you need and want, which might include a hot tub and garden. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
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  • 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

The adventurous city of Winchester awaits you

Enjoy the history and other features of Winchester. One of the city's many top draws is its golfing. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Winchester

Do you want to discover attractions to see during your stay? Venture out of your holiday home and experience everything that Winchester has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Winchester Golf Club (1.1 mi / 1.8 km)
  • Eldora Speedway (20.8 mi / 33.5 km)
  • Warm Glow Candle Company (21.6 mi / 34.8 km)
  • Abbott's Candy Shop (20.4 mi / 32.9 km)
  • Cardinal Hills Golf Course (16.5 mi / 26.6 km)
  • Trail Side Golf and Foot Golf (19.3 mi / 31 km)

Exploring the natural features in Winchester

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winchester is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Prairie Creek Reservoir and Campground (18.7 mi / 30 km)
  • Burlington Lake (18.6 mi / 29.9 km)
  • Prairie Ridge Meadow (18.9 mi / 30.4 km)
  • Big Island (20.8 mi / 33.5 km)
  • Scout Lake (21.4 mi / 34.5 km)
  • Middlefork Reservoir Park (22.7 mi / 36.6 km)

How to get to and around Winchester

The nearest airport is in Muncie, IN (MIE-Delaware County), located 21.9 mi (35.2 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?
The average price for a holiday home in Winchester is based on several factors, such as length of stay, season and property type. Whether you’re dreaming about a sprawling villa with space for extended family or an apartment perfect for just you and the kids, just add your dates of travel to see stays with amazing 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 will depend on when you’ll be there and the type and size of property you’re searching for. You can find prices quickly and easily on Stayz by entering your destination and preferred travel dates. Then use the handy filter tool to select the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.
What are the top attractions for families in Winchester?
If you’re travelling with the kids, put these family-friendly attractions in Winchester on your list of things to do:

  • Winchester Speedway
  • Winchester Golf Club

How old do you have to be to rent a holiday home in Winchester?
The minimum age can vary across properties on Stayz, so check the rules of the holiday home in Winchester you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
The length of time you can rent a holiday home in Winchester differs according to the property. Just enter your selected dates to see a list of options offering extended stays. With lots of features such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to get somewhere perfect to call your home away from home in Winchester.