Winter Short Breaks in Dorset

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Your search returned 471 cottages.

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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.8

      Outstanding

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

    Beautiful seafront apartment within the popular resort of Weymouth in Dorset. (Ref. 1003083)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 29th Nov $648

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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

    3 nights from Fri 28th Nov $525

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    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.9

      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
    • 6% off - Tue 5th Aug to 27th Aug 2025

    3 nights from Mon 5th Jan $557

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A fantastic ground-floor apartment located in West Cliff near Bournemouth, Dorset. (Ref. 1083610)

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

    3 nights from Sat 29th Nov $1932

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    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)

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

    3 nights from Sat 29th Nov $989

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    Last booked yesterday
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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)

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

    3 nights from Sat 29th Nov $634

    Secure your holiday with a 30% deposit*
    Last booked 7 hours ago
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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 28th Nov $1273

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

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

    3 nights from Sat 29th Nov $673

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    Last booked yesterday
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    • Sleeps6
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    A delightful single-storey holiday home resting in Wimborne Minster, Dorset. (Ref. 1111758)

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

    3 nights from Sat 29th Nov $578

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

      4.9

      Outstanding

    • Dream Cottages rating

    Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Fri 28th Nov $771

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