Winter Short Breaks in Dorset

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Your search returned 326 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 Tue 3rd Mar £572

    • 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 Sun 1st Mar £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 Sun 1st Mar £483

    Last booked yesterday
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2

      Good

    • Dream Cottages rating

    Two bedroom cottage close to Weymouth harbour. (Ref. 994236)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 1st Mar £392

    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. (Ref. 1114655)

    • Wi-fi
    • Washing machine

    3 nights from Sun 1st Mar £556

    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    3 nights from Tue 3rd Mar £524

    Last booked 2 days ago
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Perfect cottage to base yourself surrounded by the beautiful Dorset countryside. (Ref. 994231)

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

    3 nights from Sun 1st Mar £564

    • 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 1st Mar £406

    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      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 Sun 1st Mar £565

    • Sleeps8
    • Bedrooms5
    • PetsYes

      4.1

      Good

    • Dream Cottages rating

    Full of Character thatched cottage just outside Burton Bradstock. (Ref. 994004)

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

    3 nights from Sun 1st Mar £725

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