Winter Short Breaks in Dorset

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Your search returned 472 cottages.

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  • A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
    18
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Traditional cute cottage, in the town centre side of Weymouth harbour. (Ref. 994240)

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

    3 nights from Fri 28th Nov $626

    Secure your holiday with a 30% deposit* Book now
  • A living room with a beige sectional sofa and colorful cushions a wicker coffee table a small round white table with baked goods a lamp a chair with a pillow a dining area with wooden chairs and a table at Winkle Cottage in Weymouth
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. (Ref. 1140944)

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

    3 nights from Fri 28th Nov $677

    Secure your holiday with a 30% deposit* Book now
  • A row of terraced houses with different colored facades along a street at Old Harbour Townhouse in Weymouth
    31
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • 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 Fri 28th Nov $792

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
    23
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    3 nights from Sat 29th Nov $736

    Secure your holiday with a 30% deposit* Book now
  • A small garden with a white metal table and chairs outside a brick house with white framed windows at Elm Villa in Wareham
    34
    Wareham, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      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 Sun 30th Nov $736

    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
    29
    Broad Chalke, Wiltshire
    • 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

    3 nights from Sat 29th Nov $527

    Secure your holiday with a 30% deposit* Book now
  • A garden with red roses and a metal chair beside a brick house at The Corner House in Weymouth
    39
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. (Ref. 1129331)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov $736

    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
    27
    Puddletown, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      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 Sat 6th Dec $476

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A house with red roof and red door behind grassy hill with trees at Rempstone Farmhouse in Corfe Castle
    29
    Corfe Castle, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • 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 1st Dec $1041

    Secure your holiday with a 30% deposit* Book now
  • A garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
    27
    Cove Castle, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    2-minute walk to Sandsfoot beach and the South West Coast path. (Ref. 994582)

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

    3 nights from Sat 29th Nov $899

    Secure your holiday with a 30% deposit* Book now
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