Winter Short Breaks in Dorset

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Your search returned 483 cottages.

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    • Sleeps3
    • Bedrooms2
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    A wonderful apartment that sleeps up to three people resting in Weymouth, Dorset. (Ref. 1057385)

    • Wi-fi
    • Off-road parking
    • Washing machine
    • Baby-friendly
    • 10% off - Sat 19th Apr to 3rd May 2025

    3 nights from Sat 29th Nov £385

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

      4.7

      Outstanding

    • Dream Cottages rating

    Character cottage in Burton Bradstock, sleeping 5 people. (Ref. 994024)

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

    3 nights from Sat 29th Nov £652

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

      4.9

      Outstanding

    • Dream Cottages rating

    Stylish renovated ground floor apartment in Weymouth. (Ref. 994763)

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

    3 nights from Sat 29th Nov £620

    Secure your holiday with a 30% deposit* Book now
    • 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
    • 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* 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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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A stylish and contemporary apartment set in the town of Weymouth, Dorset. (Ref. 1072234)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov £631

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    Last booked yesterday
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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Beautifully restored, and elegantly furnished, historic cottage in Wiltshire's gorgeous Chalke Valley. (Ref. 988964)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 29th Nov £397

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    • Sleeps15
    • Bedrooms8
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. (Ref. 1003646)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sun 30th Nov £2064

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
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