Holiday Cottages in Weymouth with Swimming Pools

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Your search returned 7 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Excellent

    • Dream Cottages rating

    A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)

    • Wi-fi
    • Swimming pool
    • Dishwasher
    • Washing machine

    7 nights from £555

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    • Sleeps10
    • Bedrooms5
    • PetsNo

      4.8

      Excellent

    • Dream Cottages rating

    Luxurious 5 star contemporary property. (Ref. 993982)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from £2500

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Excellent

    • Dream Cottages rating

    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
    • Washing machine

    7 nights from £694

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    • Sleeps8
    • Bedrooms4
    • PetsNo
    • Dream Cottages rating

    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 £791

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.1

      Good

    • Dream Cottages rating

    A well-presented, modern apartment on the rugged Isle of Portland. (Ref. 1034885)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Dishwasher
    • Washing machine

    7 nights from £632

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    • Sleeps15
    • Bedrooms7
    • PetsYes

      4.0

      Good

    • Dream Cottages rating

    A spacious holiday home resting in Moreton, Dorset. (Ref. 1060785)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Games room

    7 nights from £1680

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Excellent

    • Dream Cottages rating

    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

    7 nights from £658

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Perfect for unwinding or having fun for the whole family, a holiday cottage with a swimming pool is always a popular choice among holidaymakers. Browse our selection of Weymouth cottages with swimming pools, and if you are interested please do not hesitate to book as these are amongst our most high in demand properties.

Why a holiday cottage in Weymouth with a swimming pool?

After an exhausting day rambling the South West Coast Path or exploring the attractions of Nothe Fort and the Sea Life Centre, what better way to unwind than with a dip in the hot tub or a gentle swim in your own private pool? Kids will love it too - they’ll spend endless hours splashing about and having fun, whatever the weather!  

Places to visit in Dorset

There are Dorset attractions and activities to suit all tastes, no matter where you choose to stay. Lovers of the wonderful Jurassic coastline might fancy staying in the seaside resorts of West Bay or Lyme Regis, where you can enjoy the golden sands and gentle waters as well as seeking out ancient fossils and feature landmarks.

If you’re after a rural retreat, then consider staying at the quaint village of Burton Bradstock or Lulworth, where glorious green countryside and pretty thatched cottages come in the many. 

Types of Holiday

Choose from our array of different types of holiday to find a cottage that suits you down to the ground. From dog-friendly cottages and family breaks to cottages with a sea view and those with an open fire, we hope you can find a property that ticks all your boxes. 


If you need any assistance finding a holiday cottage in Weymouth with a swimming pool, our team of friendly travel experts are ready to answer your call.