Winter Short Breaks in Dorset

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Your search returned 483 cottages.

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    • Sleeps12
    • Bedrooms6
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Beautiful converted farmhouse. (Ref. 976544)

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

    3 nights from Sat 29th Nov £1410

    Secure your holiday with a 30% deposit* Book now
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    The Cheesehouse is an exceptional, pet-friendly five-bedroom home resting in Litton Cheney, Dorset featuring a games room with pool, darts and bar area. (Ref. 1161994)

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

    3 nights from Fri 28th Nov £1360

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)

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

    3 nights from Tue 6th Jan £507

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    A well-presented barn conversion resting on the outskirts of Okeford Fitzpaine, Dorset. (Ref. 1137516)

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

    3 nights from Sat 29th Nov £592

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    This charming, two-bedroom holiday lodge rests in Bowerchalke, near Broad Chalke, Wiltshire. (Ref. 1111761)

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

    3 nights from Mon 1st Dec £539

    Secure your holiday with a 30% deposit*
    Last booked 2 hours ago
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    This fabulous Grade II listed cottage rests in the Dorset village of Marnhull. (Ref. 970616)

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

    3 nights from Mon 8th Dec £397

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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
    • £350 off - Fri 1st Aug to 29th Aug 2025

    3 nights from Sat 29th Nov £1310

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Sea Breeze is a lovely, terraced cottage resting in the outskirts of Swanage, Dorset. (Ref. 1150773)

    • Wi-fi
    • Off-road parking

    3 nights from Mon 1st Dec £430

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    Last booked 6 hours ago
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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. (Ref. 1117867)

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

    3 nights from Fri 28th Nov £392

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    3 nights from Sun 7th Dec £495

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