Winchester holiday rentals

We found 50 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Winchester that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and cable TV. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
  • 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

Find the perfect holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. One of the city's many top draws is its restaurants. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Winchester

Are you hoping to discover things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Winchester a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Melrose Vineyards (5.4 mi / 8.7 km)
  • Reustle Prayer Rock Vineyards (6.2 mi / 10.1 km)
  • Wildlife Safari (10.7 mi / 17.2 km)
  • Tesoaria Vineyard & Winery (4.6 mi / 7.4 km)
  • HillCrest Winery and Distillery (7.4 mi / 11.9 km)
  • Spangler Vineyards (9.1 mi / 14.7 km)

Exploring the natural features in Winchester

Whether you're an adventurous traveller or just want to appreciate the scenery, Winchester is a great spot to appreciate mother nature. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Stewart Park (4.3 mi / 6.9 km)
  • South Umpqua River (11.9 mi / 19.2 km)
  • Winchester Dam (0.4 mi / 0.6 km)
  • Little River (12.8 mi / 20.7 km)
  • Discovery Garden (4.3 mi / 6.9 km)
  • Central Park (8 mi / 12.8 km)

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?
Several factors can determine the price of a holiday home in Winchester, including the type of property, length of stay and season. But, all our holiday homes have one thing in common — incredible value. Just add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Winchester?
When you travel and the size and style of the property will determine the cost of your beachside holiday home. Type in your Winchester travel dates to view your available options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to select the amenities and features you want in your home.
What are the top attractions for families in Winchester?
Keeping the kids occupied during your holiday in Winchester is child’s play with these awesome family-friendly attractions:

  • Douglas County Museum of History and Natural History
  • Discovery Garden
  • Stewart Park

How old do you have to be to rent a holiday home in Winchester?
We recommend checking with the Winchester holiday home you’d like on Stayz as the age limit varies. However, it’s typically 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
The amount of time you can rent a Winchester holiday home for depends on the property. Just enter your travel dates to view options offering extended stays. They include all you require to make your extended break more comfortable and convenient, such as kitchens and laundries. Some holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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