Top Chesterfield rentals with pool or private pool - England

Explore Chesterfield rentals with pools

THE LOFT, pet friendly, character holiday cottage in Millthorpe

Sleeps 7 · 3 bedrooms · 1 bathroom

Indoor heated swimming pool - available all year round

Premier Host

Cosy Cottage with all year indoor pool, set in 9 acres of garden, amazing views

Sleeps 4 · 2 bedrooms · 1 bathroom

Premier Host

Charming cottage by a stream with trails from the doorstep in the peak district

Sleeps 4 · 2 bedrooms · 2 bathrooms

Fabulous house in the centre of Bakewell, Peak District sleeps up to 10

Sleeps 10 · 4 bedrooms · 2 bathrooms

Top rated rentals with pools - Chesterfield

Premier Host

Beautiful cottage in a great location

Quaint little cottage with great views and everything you need for a short stay. It’s just about big enough for 2 adults and 2 kids and access to the pool was a bonus. Laundry is separate and was mostly full of washing from the property during our stay. We enjoyed the short walks and expansive gardens and would be back if we lived closer.

Leighton H.

Stayed July 2025

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Frequently asked questions

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

Where you stay, when you prefer to travel and the length of your trip will influence how much you pay for a holiday home with a pool in Chesterfield. Key in your travel details on Stayz, then book the right one for you and get ready to make a splash.

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

The type of weather will help dictate when it's the ideal time to enjoy a poolside retreat. Many visitors to Derbyshire stay in a Chesterfield holiday home with a pool in February, when average temperatures range from 0.56ºC (1ºC) to 6ºC (6ºC).

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

Stayz has a range of awesome holiday homes with a pool in Chesterfield, including houses with views of historic areas. When you aren't seeing the sights, relax by going for a swim and gaze at scenes that are an attraction in themselves.