Winchester rentals with pool

We found 71 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 rentals with a pool in Winchester?
You bet. Select from 71 holiday rentals with a pool in Winchester and start your morning off with a refreshing swim before heading out to explore the sights.
How much does it cost to stay in a holiday rental with a pool in Winchester?
Indoor or outdoor pool, one bedroom or six, busy or quiet season — how much you'll pay for your Winchester stay depends on various factors. But the one consistent element? Our holiday rentals with a pool are where fun memories are made. To find a place that matches your budget, narrow your search results by the maximum nightly or total price. You can also use our "Discounts" filter to find properties that offer long-stay discounts.
When is the best time to book a holiday rental with a pool in Winchester?
With average temperatures that range from 9ºC to 20ºC, April is when many Stayz guests plan their stay. Make sure you check out our holiday rentals with a pool in this corner of Franklin County during other months too. You may find more availability if you look outside of Winchester's busier months.
What holiday rentals with a pool in Winchester have nice views?
After an eventful day out, head back to your holiday rental with a pool for a relaxing dip. The icing on the cake? Some of these Winchester stays also come with idyllic views of historic areas.
Are there holiday rentals with a private pool in Winchester?
Although there aren't any holiday rentals with a private pool in Winchester, you will find stays that have what you need to be comfortable. Picking a Stayz property means you'll have more privacy, space and home comforts compared to a hotel. And with our filter tool, you can fine-tune your search by the amenities or features you want, whether that's a barbecue or patio.
What are the top things to do in Winchester?
Tims Ford Lake, Tims Ford State Park and Tim's Ford Marina are popular attractions that'll keep the whole crew entertained in Winchester. There's nothing like a fun getaway to bring everyone together, so browse our holiday home rentals in this lively destination.
Why should I book my holiday rental with a pool with Stayz?
Whether you're travelling as a couple or with a group of pals, staying at a holiday rental with a pool promises a new level of fun and relaxation to your break. And finding a dream pad is a cinch with our handy filters. Just fine-tune your search by location, amenities, budget and more, then choose your favourite. Another excellent reason to book with us is our flexible cancellation policies. If you have to change plans, you'll get a complete refund as long as you cancel within the time frame set by the property owner.