Winter Short Breaks in Dorset

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Your search returned 457 cottages.

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    • 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 23rd Jan €1117

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

      4.6

      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 Sun 11th Jan €609

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

      4.8

      Outstanding

    • Dream Cottages rating

    Modern family house located on the edge of Weymouth, with sea views. (Ref. 994759)

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

    3 nights from Sat 21st Feb €775

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

      4.9

      Outstanding

    • Dream Cottages rating

    A high-quality, modern lodge sat on the outskirts of charming Wedmore in Somerset. (Ref. 983734)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    3 nights from Wed 21st Jan €839

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

      4.8

      Outstanding

    • Dream Cottages rating

    A character property, resting within the delightful village of Norton-sub-Hamdon. (Ref. 1000796)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 2% off - Thu 8th Jan to 27th Jan 2026

    3 nights from Fri 23rd Jan €563

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

      4.8

      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

    3 nights from Sat 7th Feb was €526 €460

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Ground Floor modern accommodation. (Ref. 994034)

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

    3 nights from Sun 11th Jan €526

    Secure your holiday with a 30% deposit* Book now
    • Sleeps8
    • Bedrooms4
    • PetsNo
    • Dream Cottages rating

    Greenwell, a delightful house located in the town of Weymouth in Dorset boasting a Smart TV, woodburning stove and proximity to the beach and pub. (Ref. 1128598)

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

    3 nights from Sun 11th Jan €1137

    Secure your holiday with a 30% deposit* Book now
    • Sleeps18
    • Bedrooms9
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. (Ref. 1123341)

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

    3 nights from Sun 11th Jan €3002

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

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

    3 nights from Sun 11th Jan €541

    Secure your holiday with a 30% deposit* Book now
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