Winter Short Breaks in Dorset

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Your search returned 490 cottages.

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. (Ref. 1096825)

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

    3 nights from Tue 9th Dec $641

    Secure your holiday with a 30% deposit*
    Last booked 7 hours ago
    Book now
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    This wave shaped lodge is architect designed and has incredible panoramic sea views from the decking. (Ref. 994765)

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

    3 nights from Fri 28th Nov $1241

    Secure your holiday with a 30% deposit* Book now
    • 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 $715

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

      4.5

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Fri 28th Nov $687

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

      4.4

      Good

    • Dream Cottages rating

    Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. (Ref. 994768)

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

    3 nights from Sat 29th Nov $630

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

      4.1

      Good

    • Dream Cottages rating

    A charming semi-detached cottage in Dorset Village of Langton Herring, close to the Jurassic coast Upside down living, WiFi. (Ref. 994488)

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

    3 nights from Fri 28th Nov $938

    Secure your holiday with a 30% deposit* Book now
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.4

      Good

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

    A tasteful, three-storey Victorian terrace cottage in the popular Dorset resort of Weymouth. (Ref. 1002126)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Sat 31st May to 28th Jun 2025

    3 nights from Fri 28th Nov $1089

    Secure your holiday with a 30% deposit* Book now
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.3

      Good

    • Dream Cottages rating

    Stanley House is an exceptional harbourside cottage located in the heart of Weymouth, Dorset. (Ref. 1138865)

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

    3 nights from Sat 29th Nov $1193

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A beautiful semi-detached barn conversion resting in Tytherleigh, Devon. (Ref. 1045057)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Washing machine

    3 nights from Mon 29th Dec $881

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

      4.8

      Outstanding

    • Dream Cottages rating

    Romantic single storey cottage in Hawkchurch. (Ref. 1020961)

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

    3 nights from Sat 29th Nov $561

    Secure your holiday with a 30% deposit* Book now
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