Winter Short Breaks in Dorset

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Your search returned 481 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • £52 off - Fri 9th May to 16th May 2025

    3 nights from Sun 30th Nov £352

    Secure your holiday with a 30% deposit* Book now
    • Sleeps13
    • Bedrooms6
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • Sky TV

    3 nights from Sat 29th Nov £1558

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    • 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

    3 nights from Fri 28th Nov £566

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Wonderfully positioned townhouse just moments from Sandsfoot beach and the South West Coast path. (Ref. 1059103)

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

    3 nights from Sat 29th Nov £737

    Secure your holiday with a 30% deposit*
    Last booked 3 hours ago
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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A beautifully presented property resting in the pretty village of Burton Bradstock. (Ref. 1069147)

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

    3 nights from Fri 28th Nov £1043

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    • Sleeps15
    • Bedrooms8
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. (Ref. 1003646)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sun 30th Nov £2062

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Lovely, well-appointed single-storey cottage near Winterborne Stickland. (Ref. 905896)

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

    3 nights from Sun 30th Nov £352

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps5
    • Bedrooms3
    • PetsNo
    • Dream Cottages rating

    Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. (Ref. 1047698)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • 5% off - Sat 12th Apr to 30th May 2025

    3 nights from Sat 29th Nov £443

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Stylishly renovated bungalow in Burton Bradstock. (Ref. 994537)

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

    3 nights from Sat 29th Nov £714

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    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. (Ref. 1091445)

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

    3 nights from Sat 29th Nov £699

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