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Winchester vacation rentals

We found 142 vacation 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 vacation rentals in Winchester that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the amenities you need and want, including WiFi and parking. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

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, yards and more
  • More for less
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Head to the charming city of Winchester

Enjoy the wineries and other features of Winchester. This romantic and relaxing city entices travelers with its coffeehouses and bars. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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 visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Winchester a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 an adventurous traveler or just want to take in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Winchester

Fly into Murrieta, CA (RBK-French Valley), the closest airport, located 9.6 mi (15.5 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying 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 vacation rental in Winchester?

The average price for a vacation rental 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 cozy 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 Center

How old do you have to be to rent a vacation rental in Winchester?

The age limit can differ between properties on Vrbo, so be sure to check the rules of the vacation home in Winchester you're interested in. But normally, it's 16, 18 or 21.

How long can I rent a vacation rental in Winchester for?

The amount of time you can book a Winchester vacation rental 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 vacation more comfortable and enjoyable, like kitchens and laundries. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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