Chesil Beach Holiday Cottages

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Your search returned 368 cottages.

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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 €552

    Secure your holiday with a 30% deposit* Book now
  • 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 €946

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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  • A row of terraced houses with white and yellow facades and a sidewalk at Brewers Quay Harbour
    29
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A delightful cottage situated next to Weymouth harbour in Dorset. (Ref. 1061726)

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

    7 nights from €943

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with white doors and windows along a narrow road with plants and flowers growing at the base of the wall at Pippins Loders in Bridport
    29
    Bridport, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Stone three bedroom cottage near Bridport. (Ref. 994548)

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

    7 nights from €828

    Secure your holiday with a 30% deposit* Book now
  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. (Ref. 932160)

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

    7 nights from €721

    Secure your holiday with a 30% deposit* Book now
  • The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Ground Floor modern accommodation. (Ref. 994034)

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

    7 nights from €518

    Secure your holiday with a 30% deposit* Book now
  • A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
    21
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Village pubs and tea rooms. (Ref. 994358)

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

    7 nights from €564

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  • A sitting area with two sofas and a dining table with chairs overlooking the sea at Sandpiper Chalet in Eype
    28
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming single-storey holiday home nestled in the quaint village of Eype, Dorset. (Ref. 1078226)

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

    7 nights from €617

    Secure your holiday with a 30% deposit* Book now
  • A row of white houses with small front gardens and brick walls along a street at Brambles in West Bay
    40
    West Bay, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Brambles is a stylish, three-bedroom property located in West Bay in Dorset, enjoying a pet-friendly policy and only a short walk to a beach. (Ref. 1167423)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from €895

    Secure your holiday with a 30% deposit* Book now
  • A row of three terraced houses with brick and white exteriors with small front gardens at Quay Cottage in Weymouth
    29
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Quay cottage is a period terraced property in Weymouth. (Ref. 994576)

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

    7 nights from €678

    Secure your holiday with a 30% deposit* Book now
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