Top Winchcombe rentals with pool or private pool - Cheltenham

Explore Winchcombe rentals with pools

Queens Cottage at Sudeley Castle, Bolthole Retreats

A sudeley castle cottage that sleeps 6 guests in 2 bedrooms

Sleeps 6 · 2 bedrooms · 2 bathrooms

Vineyard Street with no.6 on this side of the road.

Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe.

Sleeps 4 · 2 bedrooms · 1 bathroom

Top rated rentals with pools - Winchcombe

Premier Host

Lovely cottage and great location

The cottage was only a few minutes walk away from the heart of the beautiful village and was a perfect “home away from home” after travelling around Europe for several weeks. Cooking some home cooked meals and catching up on some laundry was well needed and well catered for and very central to all the area has to offer from a tourist perspective. I highly recommend!

Lyndal C.

Stayed July 2025

Delightful Cotswolds Cottage

Beautiful in every way. Lovely hosts on a gorgeous property. Peaceful and comfortable, a lovely stay.

Katrina P.

Stayed Dec 2024

Your very own detached Cottage with off street parking, cottage garden and Well.

Premier Host

Beautiful cottage, close to everything yet quiet

Perfectly positioned and equipped - particularly grateful for the wonderful loaf of bread and marmalade welcoming us on our arrival, graciously provided by our hosts!

Susan W.

Stayed Mar 2024

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Frequently asked questions

How much does it cost to stay in a holiday home with a pool in Winchcombe?

Lap pool or plunge pool, one bedroom or six, low season or peak season — how much you'll pay for your Winchcombe stay is influenced by all sorts of variables. But one thing that remains consistent? Our holiday homes with a pool are where fun memories are made. To find a getaway that suits 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 savings on longer stays.

When is the best time to book a holiday home with a pool in Winchcombe?

Consider booking your poolside adventure to Winchcombe in February, when the average temperature is between 2ºC (2ºC) and 7ºC (7ºC). This is the most popular time for Stayz guests to get a holiday home with a pool in this destination, which is located in Cheltenham.

What holiday homes with a pool in Winchcombe have nice views?

Stayz has some superb holiday homes with a pool in Winchcombe, including houses with views of historic areas. Before and after seeing the sights, relax by taking a dip and gaze at vistas that are an attraction in themselves.