Chesil Beach Holiday Cottages

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Your search returned 359 cottages.

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  • An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
    33
    Ringstead, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    This quirky, converted bunker rests in Ringstead near Preston, Dorset. (Ref. 1131689)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher

    7 nights from $1157

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  • A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
    23
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $809

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  • A street view showing old and new boathouse buildings and inner harbour with boats in the background at Old Boathouse Weymouth
    23
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Centrally located in Weymouth beautiful holiday home for family or friends. (Ref. 994461)

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

    7 nights from $859

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  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from $656

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  • Front of a red brick terraced house with white door and windows and plants in front at Rockpools in Weymouth
    Property has offers
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Sleeping four in Maltings area of Weymouth, pet friendly. (Ref. 994596)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    • $274 off - Sat 1st Aug to 8th Aug 2026

    7 nights from $726

    Last booked 2 days ago
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  • An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth
    16
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A cosy stone cottage for two this is the ideal place to spend quality time together, walking and exploring the local area. (Ref. 994208)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $691

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  • A row of brick terraced houses with bay windows and small front gardens at Covecastle Cottage in Weymouth
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. (Ref. 994072)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $715

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  • A brick house with a black front door and three windows with gravel and plants in the front garden at The Pines in Weymouth
    28
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Tucked in a quiet location in Weymouth, The Pines is a modern holiday home for families or couples. (Ref. 994549)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $937

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  • The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
    26
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from $715

    Last booked 2 days ago
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  • A house with outdoor seating area at Budmouth Upwey near Weymouth
    42
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. (Ref. 932157)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $803

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