Photo by Betsy Wood

Winchester rentals with pool

We found 104 rentals with pool — enter your dates for availability

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

Frequently asked questions

Are there any holiday homes with a pool in Winchester?
Book one of our six holiday homes with a pool in Winchester and get ready for a splashing good time. Four Seasons, Romoland and Sun City are among the city's best areas to stay.
How much does it cost to stay in a holiday home with a pool in Winchester?
If you'd love to grab a deal on your holiday home with a pool, our filters are there to help. After your initial search, narrow down your results according to your preferences, including location, total price and features and amenities. We've got accommodation in Winchester for all sorts of budgets, so make the most of our filters to find the perfect stay.
When is the best time to book a holiday home with a pool in Winchester?
If you want to visit Winchester at one of its busiest times, plan your escape for January. That's when temperatures range from around 6 ºC (6ºC) to 18 ºC (18ºC), and when many Bookabach guests unwind in a holiday home with a pool in this destination. Of course, there are other excellent times to visit this corner of Riverside County, so do some homework into which season or month best fits your plans.
What holiday homes with a pool in Winchester have nice views?
Stay at a holiday home with a pool in Winchester and you can spend your break switching between taking dips and gazing out at stunning vistas. Some of our more popular home houses here offer views of historic areas.