Winter Short Breaks in Dorset

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Your search returned 477 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Modern and spacious cottage for couples or family in the Isle of Portland. (Ref. 994497)

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

    3 nights from Sat 28th Feb £638

    Secure your holiday with a 30% deposit* Book now
    • Sleeps15
    • Bedrooms8
    • PetsYes

      4.8

      Outstanding

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

    Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. (Ref. 1003646)

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

    3 nights from Sun 30th Nov £1970

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    3 nights from Tue 2nd Dec £427

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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 Fri 5th Dec was £427 £353

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    A lovely two-bedroom bungalow resting in Preston, Dorset. (Ref. 1106680)

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

    3 nights from Sat 29th Nov £590

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Cosy property located in the coastal village of West Bexington. (Ref. 994761)

    • Off-road parking
    • Ground floor bedroom
    • Washing machine

    3 nights from Sat 29th Nov £427

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    Last booked yesterday
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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    A Grade II listed former stable located in Colyton, in Devon, near to the Jurassic coast and beautiful countryside. (Ref. 1059490)

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

    3 nights from Fri 28th Nov £389

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    A charming Victorian dwelling resting in the town of Wareham, Dorset. (Ref. 1053728)

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

    3 nights from Fri 28th Nov £592

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    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    3 nights from Fri 28th Nov £670

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A delightful, single-storey home resting in Stockland near Honiton, Devon. (Ref. 1131012)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • 2% off - Mon 10th Nov to 31st Dec 2025

    3 nights from Fri 28th Nov £462

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
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