Winter Short Breaks in Dorset

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Your search returned 482 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. (Ref. 1129331)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 28th Nov £566

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

      4.7

      Outstanding

    • Dream Cottages rating

    Generous second floor apartment with spectacular sea views. (Ref. 993990)

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

    3 nights from Fri 28th Nov £627

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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 £413

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    3 nights from Sat 29th Nov £608

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. (Ref. 994321)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Sat 31st May to 14th Jun 2025

    3 nights from Sun 30th Nov £396

    Secure your holiday with a 30% deposit*
    Last booked 9 hours ago
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. (Ref. 1097676)

    • Wi-fi

    3 nights from Sun 30th Nov £421

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A well-positioned, three-storey property resting in Weymouth, Dorset. (Ref. 1118939)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 30th Nov £442

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    • Sleeps2
    • Bedrooms1
    • PetsNo
    • Dream Cottages rating

    The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. (Ref. 1165359)

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

    3 nights from Sat 29th Nov £305

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. (Ref. 994072)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 28th Nov £515

    Secure your holiday with a 30% deposit* Book now
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

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

    3 nights from Sat 29th Nov £447

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