Winter Short Breaks in Dorset

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Your search returned 480 cottages.

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  • A thatched roof cottage next to a white building with parking spaces near trees at Thimble Cottage in Winterborne Stickland near Blandford Forum
    24
    Save £60 with code BFDEAL60
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    This charming, one-bedroom holiday home rests in Winterborne Stickland near Blandford Forum, Dorset. (Ref. 1068261)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sun 30th Nov £520

    Secure your holiday with a 30% deposit*
    Last booked 2 hours ago
    Book now
  • The exterior of a modern white apartment building with balconies and a pathway surrounded by grass and plants at 1 Blue Waters in Southbourne
    29
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A lovely, single level lower-ground-floor apartment resting in Southbourne, Dorset. (Ref. 1095373)

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

    3 nights from Sun 30th Nov £536

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a brick cottage with green front door and multiple white windows at Millers Cottage in Puddletown
    Property has offers
    32
    Save £60 with code BFDEAL60
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Miller’s Cottage is a snug and romantic dwelling located in the village of Puddletown, nearby a river in Dorset, with a woodburning stove and welcoming one pet. (Ref. 1160443)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 5th Dec was £464 £359

    Secure your holiday with a 30% deposit*
    Last booked 1 hour ago
    Book now
  • A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
    Property has offers
    42
    Save £60 with code BFDEAL60
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    3 nights from Sat 6th Dec was £780 £608

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • An outdoor area with a table and umbrella at Corner Barn in Winterborne Stickland
    33
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

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

    3 nights from Wed 3rd Dec £388

    Secure your holiday with a 30% deposit* Book now
  • A patio with a round table and two chairs with two mugs on the table overlooking a gravel area and green hills at Burton Bay in Burton Bradstock
    Property has offers
    20
    Save £60 with code BFDEAL60
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Pets welcome. (Ref. 994050)

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

    3 nights from Sat 13th Dec £497

    Secure your holiday with a 30% deposit* Book now
  • A garden with plants and flowers in front of a stone house with skylights at Kings Cottage - North in Broad Chalke
    Property has offers
    29
    Save £60 with code BFDEAL60
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Beautifully restored, and elegantly furnished, historic cottage in Wiltshire's gorgeous Chalke Valley. (Ref. 988964)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • 5% off - Tue 23rd Dec to 30th Dec 2025

    3 nights from Sun 30th Nov £397

    Secure your holiday with a 30% deposit* Book now
  • The driveway and entrance of a house with trees plants a small shed and a black cat at Nuthatch in Honiton
    Property has offers
    15
    Save £60 with code BFDEAL60
    • 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 Sun 7th Dec £462

    Secure your holiday with a 30% deposit* Book now
  • A row of modern brick and beige townhouses with balconies and large windows behind a green hedge at Kiama in Weymouth
    30
    Save £60 with code BFDEAL60
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A well-positioned, three-storey property resting in Weymouth, Dorset. (Ref. 1118939)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 30th Nov £442

    Secure your holiday with a 30% deposit* Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    29
    Save £60 with code BFDEAL60
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9

      Outstanding

    • 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 Sat 3rd Jan £576

    Secure your holiday with a 30% deposit*
    Last booked 3 hours ago
    Book now
Most relevant
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