Winter Short Breaks in Dorset

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Your search returned 483 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    This quirky, converted bunker rests in Ringstead near Preston, Dorset. (Ref. 1131689)

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

    3 nights from Tue 6th Jan £882

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Pets welcome. (Ref. 994050)

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

    3 nights from Fri 28th Nov £475

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

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

    3 nights from Sat 29th Nov £508

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    Last booked yesterday
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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

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    A bright and airy lodge resting in Osmington near Preston, Dorset. (Ref. 1093891)

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

    3 nights from Fri 28th Nov £669

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    3 nights from Fri 28th Nov £594

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    3 nights from Fri 28th Nov £714

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    • Sleeps6
    • Bedrooms3
    • PetsYes
    • Dream Cottages rating

    The Swanage Rail Lookout is a newly refurbished picturesque detached house boasting an enclosed garden, perfect for those with or without pets looking for a walking distance seaside holiday and/or train enthusiasts! (Ref. 1157056)

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

    3 nights from Fri 5th Dec was £814 £617

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    • 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 £637

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    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A traditional farmhouse on the cliff top in Burton Bradstock, close to Hive Beach and it’s renowned café, West Bay, Wifi. (Ref. 994095)

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

    3 nights from Sat 29th Nov £413

    Secure your holiday with a 30% deposit* Book now
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