Dorset Family Holidays

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Your search returned 396 cottages.

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  • An outdoor patio with a table and chairs overlooking a garden and sea at Blue Yonder in Weymouth
    37
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Blue Yonder is a cheerful, terrace holiday home resting by the sea in Weymouth, Dorset. (Ref. 1144628)

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

    7 nights from $792

    Secure your holiday with a 30% deposit* Book now
  • A patio with outdoor dining furniture and hot tub next to a lawn and wooden house at The Gully in Sherborne
    45
    Sherborne, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A superb four-bedroom barn conversion resting in Hummer, Dorset. (Ref. 1086608)

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

    7 nights from $1850

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A backyard with a green lawn a patio dining set with an umbrella and a house with large windows and a sloped roof at Kings Cottage - South in Broad Chalke
    52
    Broad Chalke, Wiltshire
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Exceptional, lovingly restored cottage in Wiltshire's beautiful Chalke Valley. (Ref. 988982)

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

    7 nights from $1418

    Secure your holiday with a 30% deposit* Book now
  • A row of white and grey terraced houses with bushes and purple flowers in front at Bay Tree House in Seaton Devon
    61
    Seaton, Devon, Devon
    • Sleeps16
    • Bedrooms8
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautiful four-storey townhouse resting in the seaside town of Seaton, Devon. (Ref. 1063005)

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

    7 nights from $2437

    Secure your holiday with a 30% deposit* Book now
  • A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
    43
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • 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 $982

    Secure your holiday with a 30% deposit* Book now
  • A cottage with a thatched roof and a garden at Happiness Cottage in Piddlehinton
    Property has offers
    35
    Piddlehinton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    Happiness Cottage is a character cottage with a contemporary style, woodburning stove and enclosed garden resting in the village of Piddlehinton in Dorset. (Ref. 1175141)

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

    • 10% off - Fri 24th Oct to 12th Dec 2025

    7 nights from $665

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    7 nights from $775

    Secure your holiday with a 30% deposit* Book now
  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    7 nights from $938

    Secure your holiday with a 30% deposit* Book now
  • A small garden patio with a black table and four chairs in front of a blue house with open double doors at Gone Sailing Brewers Quay Harbour
    26
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Two bedroom cottage. (Ref. 994229)

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

    7 nights from $706

    Secure your holiday with a 30% deposit* Book now
  • A window view of a harbor with sailboats and buildings in the background at The Ferryman in Weymouth
    16
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A character-filled cottage located in the popular seaside town of Weymouth, Dorset. (Ref. 1017295)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $775

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
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