Winter Short Breaks in Dorset

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Your search returned 480 cottages.

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    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    An attractive, converted Victorian school resting within Piddletrenthide. (Ref. 933650)

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

    3 nights from Fri 28th Nov $715

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Dream Cottages rating

    Vine Cottage is a beautiful 17th-century stone cottage tucked away in the heart of the charming village of Burton Bradstock, Dorset. (Ref. 1189482)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Fri 28th Nov $619

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

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

    3 nights from Sat 6th Dec $522

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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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 $720

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    This cosy lodge on a peaceful15 acre site, is resting near village of Milton on Stour in Dorset. (Ref. 967741)

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

    3 nights from Sat 29th Nov $555

    Secure your holiday with a 30% deposit* Book now
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.9

      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 $925

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A pretty little modern house just a few minutes walk from the harbourside and local amenities. (Ref. 993929)

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

    3 nights from Fri 28th Nov $747

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 29th Nov $833

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    • Sleeps7
    • Bedrooms4
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Four bedrooms in Kellaway Court, Weymouth. (Ref. 994219)

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

    3 nights from Fri 28th Nov $1050

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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    • Sleeps13
    • Bedrooms6
    • PetsNo

      5.0

      Perfect

    • 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
    • 20% off - Sun 9th Nov to 1st Dec 2025

    • 20% off - Mon 1st Dec to 21st Dec 2025

    3 nights from Mon 1st Dec $2091

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
Most relevant
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  • Sleeps (highest first)
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