Winter Short Breaks in Dorset

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Your search returned 492 cottages.

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    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.3

      Good

    • Dream Cottages rating

    A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. (Ref. 993976)

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

    3 nights from Fri 28th Nov $1568

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

      4.7

      Outstanding

    • Dream Cottages rating

    Absolutely stunning, luxurious ground floor accommodation at the eastern end of Wiltshire's beautiful Chalke Valley. (Ref. 1016405)

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

    3 nights from Fri 28th Nov $1282

    Secure your holiday with a 30% deposit* Book now
    • 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 $649

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. (Ref. 1146011)

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

    3 nights from Sun 30th Nov $714

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    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • 5% off - Fri 7th Mar 2025 to 30th Apr 2026

    3 nights from Mon 1st Dec $6290

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

      4.9

      Outstanding

    • Dream Cottages rating

    A beautifully presented property located in peaceful village of Burton Bradstock. (Ref. 1069215)

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

    3 nights from Sat 29th Nov $887

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. (Ref. 1159836)

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

    3 nights from Fri 28th Nov $797

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A stylish and contemporary period home near Brewers Quay, Weymouth. (Ref. 1109892)

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

    3 nights from Fri 28th Nov $774

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Lovely thatched Grade II listed cottage for a family or friends. (Ref. 994302)

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

    3 nights from Fri 28th Nov $921

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Directly on the seafront. (Ref. 993989)

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

    3 nights from Fri 28th Nov $888

    Secure your holiday with a 30% deposit* Book now
Most relevant
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  • Price (lowest first)
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  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
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