Dorset Family Holidays

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Your search returned 396 cottages.

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  • A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
    17
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    7 nights from £714

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a stone house with wooden windows and door on a gravel ground at The Stables Burton Bradstock
    31
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property located in peaceful village of Burton Bradstock. (Ref. 1069215)

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

    7 nights from £932

    Secure your holiday with a 30% deposit* Book now
  • A coastal view with boats on water and a hill in the background at Portland Pebble in Wyke Regis
    43
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    An enticing, semi-detached house sitting in Wyke Regis, Dorset. (Ref. 1097679)

    • Wi-fi
    • Off-road parking

    7 nights from £708

    Secure your holiday with a 30% deposit* Book now
  • A detached house with a double garage and driveway at Connaught Gardens in Weymouth
    29
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Large, modern house nestled on the outskirts of Weymouth, 1 mile from the beach and restaurants. (Ref. 1001446)

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

    7 nights from £852

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • Front of a red brick terraced house with white door and windows and plants in front at Rockpools in Weymouth
    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

    7 nights from £567

    Secure your holiday with a 30% deposit* Book now
  • A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
    46
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fabulous three-bedroom holiday home in Wyke Regis, Dorset. (Ref. 1103441)

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

    7 nights from £728

    Secure your holiday with a 30% deposit* Book now
  • A cottage with a patio and garden at Droop Farm Cottage in Droop near Hazelbury Bryan
    44
    Droop near Hazelbury Bryan, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A superb, Grade II listed cottage built of local stone and set deep in the Dorset countryside. (Ref. 988951)

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

    7 nights from £707

    Secure your holiday with a 30% deposit* Book now
  • Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth
    19
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A terrace property resting close to the beach and harbour in Weymouth. (Ref. 1038344)

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

    7 nights from £594

    Secure your holiday with a 30% deposit* Book now
  • 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 £628

    Secure your holiday with a 30% deposit* Book now
  • A kitchen with white cabinets marble countertops skylights and floral curtains at Upsidedown House Brewers Quay Harbour
    Property has offers
    25
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Located in a quiet location in Weymouth, Upsidedown House is a unique and beautiful holiday home. (Ref. 994746)

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

    • £294 off - Mon 29th Dec 2025 to 6th Jan 2026

    7 nights from £912

    Secure your holiday with a 30% deposit* Book now
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