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Winchester holiday rentals

We found 141 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 24 homes and other holiday rentals in Winchester that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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

Head to the charming city of Winchester

Enjoy the wineries and other features of Winchester. This romantic and relaxing city entices travellers with its coffee shops and bars. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Winchester

Do you want to discover attractions to see in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Soboba Springs Country Club (10.8 mi / 17.4 km)
  • Wilson Creek Winery (11.5 mi / 18.4 km)
  • Ponte Winery (12.1 mi / 19.4 km)
  • Rancho Palomar Winery (12.6 mi / 20.4 km)
  • Callaway Vineyard and Winery (13 mi / 21 km)
  • Thorton Winery (13.1 mi / 21 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winchester is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Diamond Valley Lake Marina (4.6 mi / 7.4 km)
  • Lake Perris (11.4 mi / 18.3 km)
  • Lake Perris State Recreation Area (11.7 mi / 18.8 km)
  • Lake Elsinore (15.7 mi / 25.2 km)
  • Grand Tradition Estate and Gardens (25.6 mi / 41.2 km)
  • Moreno Beach (12.1 mi / 19.5 km)

Travelling to and around Winchester

Fly into Murrieta, CA (RBK-French Valley), the closest airport, located 9.6 mi (15.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into San Bernardino, CA (SBD-San Bernardino Intl.), which is 28.6 mi (46 km) away.

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 length of stay, season and property type. Whether you'd like a sprawling villa with lots of bedrooms or a cosy cottage that's perfect for two, just add your travel dates to see stays with unbeatable value.

How much does it cost to rent a beach house in Winchester?

When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Click on your Winchester travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to pick the features and amenities you need.

What are the top attractions for families in Winchester?

There are lots of exciting things to do and see with the family in Winchester, such as:

  • Orange Empire Railroad Museum
  • Ramona Bowl Amphitheatre
  • Western Science Centre

How old do you have to be to rent a holiday home in Winchester?

The age limit can differ between properties on Vrbo, so be sure to check the rules of the holiday home in Winchester you're interested in. But normally, 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 is up to the property. Just put in your dates of travel to browse options that offer long-term stays. They feature everything you need to make your extended holiday more comfortable and enjoyable, like kitchens and laundries. Some holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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