Your search returned 13 cottages.
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- Sleeps8
- Bedrooms4
- PetsNo
16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)
- Wi-fi
- Swimming pool
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £810
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- Sleeps12
- Bedrooms5
- PetsYes
Luxurious 5 star contemporary property. (Ref. 993982)
- Wi-fi
- Off-road parking
- Swimming pool
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
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£955 off - Sat 16th May to 23rd May 2026
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£312 off - Sat 6th Jun to 13th Jun 2026
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£367 off - Sat 13th Jun to 20th Jun 2026
7 nights from £3550
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- Sleeps15
- Bedrooms8
- PetsYes
Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. (Ref. 1003646)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
7 nights from £2317
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- Sleeps4
- Bedrooms2
- PetsNo
A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)
- Wi-fi
- Swimming pool
- Dishwasher
- Washing machine
7 nights from £561
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- Sleeps8
- Bedrooms4
- PetsYes
Beautiful barn conversion positioned in the lovely village of Dewlish in Dorset. (Ref. 1003641)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
7 nights from £837
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- Sleeps4
- Bedrooms2
- PetsNo
Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. (Ref. 12497)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Washing machine
- Baby-friendly
7 nights from £620
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- Sleeps4
- Bedrooms2
- PetsNo
Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. (Ref. 12494)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £677
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- Sleeps10
- Bedrooms5
- PetsYes
Bredy Cottages is an imaginatively extended 4-bedroom cottage with a handy open-plan living area, a snug with a woodburning stove, and pretty gardens. (Ref. 1176478)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £1460
Book nowLast booked yesterday -
- Sleeps15
- Bedrooms7
- PetsYes
A spacious holiday home resting in Moreton, Dorset. (Ref. 1060785)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
7 nights from £2211
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- Sleeps8
- Bedrooms4
- PetsYes
Bredy Cottages is an imaginatively extended 4-bedroom cottage in the outskirts of Burton Bradstock, Devon, with a woodburning stove. (Ref. 1200771)
- Wi-fi
- Off-road parking
- Swimming pool
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £1320
Access to your very own private swimming pool adds the real ‘wow’ factor to any holiday. We have a select range of beautiful properties, boasting either outdoor or indoor private heated swimming pools throughout Dorset.
Choosing a Dorset Holiday Cottages with a Pool
Children love nothing more than playing in a pool all day, which in turn gives parents the opportunity to sit watching, with a glass of prosecco in hand.
Perhaps you could even use your holiday to teach the little ones to swim. Either way, the addition of a swimming pool makes for memorable holidays the whole family can enjoy.
Some of our Dorset cottages boast outdoor pools and are also just a short trip to the beach.
The Jurassic coastline is never too far away from any of our cottages and to having the choice between your own pool and a sunny, golden beach means entertaining the children has never been so easy.
Holiday Homes in Dorset with Pool
A relaxing swim can help guests of all ages to unwind, whether you choose to use your pool to get some laps in before you head out for the day.
Or, for a quick dip to cool down when the sun is at its hottest, the Jurassic Coast is known to have one of the best sun records in the country, after all.
Finding the Perfect Dorset Cottages with a Pool
These cottages are dotted across Dorset in pretty coastal villages, near to old picturesque harbours, next to historic market towns and tucked away deep in the countryside.
There is so much to do in this wonderful county. Why not spend the day exploring and then return home to dine in the comfort of your very own Dorset holiday cottage with a pool?
Browse our collection of Dorset cottages with a pool today or get in touch and one of our travel experts will be able to assist you further.