Winter Short Breaks in Dorset

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Your search returned 473 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Dream Cottages rating

    The Old Flax Shop is a glorious Grade II listed annex in the town of Bridport, Dorset, boasting a woodburning stove and views over the iconic Colmers Hill. (Ref. 1175564)

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

    3 nights from Fri 28th Nov €656

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

      4.7

      Outstanding

    • Dream Cottages rating

    A delightful two-bedroom ground-floor apartment resting in Swanage, Dorset. (Ref. 1093320)

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

    3 nights from Sat 29th Nov €745

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

      4.3

      Good

    • Dream Cottages rating

    Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. (Ref. 1091449)

    • Wi-fi
    • Off-road parking
    • Washing machine
    • 20% off - Sat 28th Jun to 4th Jul 2025

    3 nights from Fri 28th Nov €619

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    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    3 nights from Fri 28th Nov €848

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2

      Good

    • Dream Cottages rating

    Located in the village of Corfe Castle, Tavern Way is a lovely home for families or couples. (Ref. 994715)

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

    3 nights from Fri 28th Nov €637

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Exceptional, spacious rural barn conversion. (Ref. 905897)

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

    3 nights from Sat 29th Nov €481

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Lovely early Victorian style Grade II listed cottage set in Warmwell village. (Ref. 994760)

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

    3 nights from Sat 29th Nov €637

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      3.9

      Good

    • Dream Cottages rating

    A modern harbourside apartment with views over the town bridge and harbour from all windows. (Ref. 994242)

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

    3 nights from Fri 28th Nov €733

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. (Ref. 1162204)

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

    3 nights from Sat 29th Nov €577

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    This wave shaped lodge is architect designed and has incredible panoramic sea views from the decking. (Ref. 994765)

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

    3 nights from Fri 28th Nov €1116

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
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