Holiday Cottages in Weymouth with Swimming Pools

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  • Baytree Lodge

    Osmington, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsNo
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    Luxurious 5 star contemporary property. Games room. Indoor swimming pool. WiFi. Stunning views. Five en-suite bedrooms, one family bathroom. Large sitting room and generous sitting/dining room/kitchen. (Ref. 993982)

    7 nights from £1782

  • Old Higher Lighthouse Branscombe Lodge

    Portland Bill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

    7 nights from £522

  • Old Higher Lighthouse Stopes Cottage

    Portland Bill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
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    Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

    7 nights from £570

    Last booked 7 hours ago
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  • Rafters

    West Lulworth, Dorset
    • Sleeps20
    • Bedrooms10
    • PetsNo
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    An incredibly well-presented thatched cottage with stunning sea views. Located in the picturesque village of Lulworth with ten en-suite bedrooms. Indoor pool, games room and cinema room. Ample private driveway parking. Wareham 9.6 miles. (Ref. 1037282)

    7 nights from £13880

  • Beaumont Village 14 at Silverlake

    Warmwell, Dorset
    • Sleeps10
    • Bedrooms4
    • PetsNo
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    Perfect for large families or group of friends. Wood burner. Sleeps 10. Access to on-site facilities. WiFi. Parking. Set in 100’s acres of secure estate. (Ref. 994060)

    7 nights from £1009

  • Beaumont Village 7 at Silverlake

    Warmwell, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo
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    Parking for 2 cars. Detached 3 bed cottage with WiFi. onsite Spa, swimming pool and outdoor activities. Perfect for a family or group of friends. (Ref. 994065)

    7 nights from £859

  • Beaumont Village 9 at Silverlake

    Warmwell, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo
    • Rating

    A contemporary sleep 8 house, on the lakeside, on site pool and SPA, nature reserve walks. Roof terrace, BBQ Wifi. (Ref. 994067)

    7 nights from £1022

  • Bulrushes

    Warmwell, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo
    • Rating

    Modern contemporary home, sleeps 8, with swimming pool and nature reserve. (Ref. 994064)

    7 nights from £959

  • Pennsylvania Castle

    Wakeham, Portland, Dorset
    • Sleeps20
    • Bedrooms9
    • PetsNo
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    Remarkable five star gold castle dominating the coastline on the Isle of Portland, Dorset. Sea views. En-suite bedrooms. Swimming pool. WiFi. Private parking. Close to beach, shops and pub. (Ref. 1003700)

    7 nights from £10473

  • Beaumont Village 8 at Silverlake

    Warmwell, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo
    • Rating

    A contemporary and modern sleep 8 house, with lake views, bifold doors, wood burner, access to onsite activities hub, Spa and swimming pool. (Ref. 994066)

    7 nights from £1009

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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.