Winter Short Breaks in Dorset

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Your search returned 481 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    A charming chalet-style bungalow resting within the town of West Bay. (Ref. 1013337)

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

    3 nights from Sat 29th Nov £688

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    3 nights from Sat 29th Nov £487

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    3 nights from Sun 30th Nov £608

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    This charming, two-bedroom holiday lodge rests in Bowerchalke, near Broad Chalke, Wiltshire. (Ref. 1111761)

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

    3 nights from Mon 1st Dec £539

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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Lovely apartment nestled in the thriving Dorest town of Swanage. (Ref. 979371)

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

    3 nights from Fri 28th Nov £358

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in a stunning loaction overlooking hills in Dorset. (Ref. 994654)

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

    3 nights from Sat 29th Nov £742

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)

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

    3 nights from Fri 28th Nov £874

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    • Sleeps7
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. (Ref. 1091335)

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

    3 nights from Sun 30th Nov £642

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    Last booked 2 days ago
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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Beamed, single-storey holiday cottage near Winterborne Stickland. (Ref. 905898)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • £82 off - Fri 23rd May to 30th May 2025

    • £42 off - Fri 30th May to 6th Jun 2025

    • £48 off - Fri 6th Jun to 13th Jun 2025

    • £62 off - Fri 13th Jun to 20th Jun 2025

    3 nights from Sat 29th Nov £350

    Secure your holiday with a 30% deposit*
    Last booked today
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    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Modern family house located on the edge of Weymouth, with sea views. (Ref. 994759)

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

    3 nights from Fri 28th Nov £627

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