Holiday Cottages for October Half term

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Your search returned 424 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. (Ref. 1169819)

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

    3 nights from Fri 23rd Oct £572

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Traditional Portland Cottage. (Ref. 993922)

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

    3 nights from Fri 23rd Oct £529

    Last booked 2 days ago
    Book now
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    3 nights from Fri 23rd Oct £688

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4

      Good

    • Dream Cottages rating

    A pretty, renovated terraced cottage, close to the old harbour and Brewers Quay in Weymouth. (Ref. 1043009)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 23rd Oct £592

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2

      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
    • 15% off - Wed 18th Feb to 30th Apr 2026

    3 nights from Tue 27th Oct £483

    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    A boutique, period home moments from Weymouth's iconic harbour. (Ref. 1177943)

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

    3 nights from Thu 29th Oct £497

    • Sleeps6
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    A bright, ground-floor apartment resting in the lively seaside town of Bournemouth, Dorset. (Ref. 1128806)

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

    3 nights from Sun 25th Oct £619

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Pendennis, a charming listed cottage in the heart of the beautiful town of Sherborne, Dorset. (Ref. 1148488)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sun 25th Oct £406

    Last booked yesterday
    Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Honeypot Cottage is a conventional, three-storey cottage situated near Swanage Beach in Swanage, Dorset, boasting a Smart TV and enclosed courtyard. (Ref. 1164485)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Wed 28th Oct £565

    Last booked 2 days ago
    Book now
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Old Harry Cottage is a delightful detached holiday home, with off-road parking, resting in the coastal town of Swanage in Dorset close to the beach. (Ref. 1162887)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • 50% off - Fri 23rd Jan to 1st Apr 2026

    3 nights from Fri 30th Oct £555

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