Winter Short Breaks in Dorset

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Your search returned 471 cottages.

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    An eye-catching stone cottage resting on the outskirts of Shaftesbury, Dorset. (Ref. 1008394)

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

    3 nights from Mon 15th Dec $472

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

      5.0

      Perfect

    • Dream Cottages rating

    The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. (Ref. 1165359)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • 20% off - Sat 20th Dec 2025 to 2nd Jan 2026

    • 10% off - Sat 3rd Jan to 31st Jan 2026

    3 nights from Thu 1st Jan $408

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

    June Cottage is a lovely cottage situated on the outskirts of Wool in Dorset, allowing pets and is well-situated to nearby attractions and amenities. (Ref. 1181945)

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

    3 nights from Mon 15th Dec $723

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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 Mon 15th Dec $687

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      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 Mon 15th Dec $797

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    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    Cedar Drive is a charming house in Preston, Dorset, boasting ground-floor living, close proximity to local amenities and the coast for great days out. (Ref. 1173784)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Washing machine
    • 10% off - Mon 22nd Dec to 29th Dec 2025

    • 10% off - Mon 29th Dec 2025 to 5th Jan 2026

    3 nights from Mon 15th Dec $666

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    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

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

    3 nights from Mon 15th Dec $1348

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Rempstone Farmhouse, a delightful, detached holiday home resting near Corfe Castle in Dorset. (Ref. 1155019)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Washing machine
    • Games room

    3 nights from Mon 15th Dec $1199

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    Last booked 1 hour ago
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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    Two bedroom cottage. (Ref. 994229)

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

    3 nights from Mon 15th Dec $715

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    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    Directly on the seafront. (Ref. 993989)

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

    3 nights from Mon 15th Dec $888

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