Winter Short Breaks in Dorset

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Your search returned 473 cottages.

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  • An outdoor seating area with a table and two chairs outside a small stone building at The Studio in Shaftesbury
    24
    Shaftesbury, Dorset
    • 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 Sat 29th Nov $478

    Secure your holiday with a 30% deposit* Book now
  • A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    3 nights from Sat 29th Nov $659

    Secure your holiday with a 30% deposit* Book now
  • A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
    42
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      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 Fri 28th Nov $809

    Secure your holiday with a 30% deposit* Book now
  • Stone cottage house with white door and windows surrounded by bushes at The Old Reading Room in Langton Herring
    40
    Langton Herring, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A charming semi-detached cottage in Dorset Village of Langton Herring, close to the Jurassic coast Upside down living, WiFi. (Ref. 994488)

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

    3 nights from Fri 28th Nov $952

    Secure your holiday with a 30% deposit* Book now
  • Stone house with wooden door and four windows and plants in front at Norden House in Maiden Newton
    29
    Maiden Newton, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A character filled property resting in the pretty village of Maiden Netwon in Dorset. (Ref. 1072294)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 29th Nov $957

    Secure your holiday with a 30% deposit* Book now
  • Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
    42
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)

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

    3 nights from Fri 28th Nov $1280

    Secure your holiday with a 30% deposit* Book now
  • The front entrance of a building with a dark door numbered 38 and a curved window with plants along the path at Flat 2 38 Preston Road Weymouth
    29
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1037083)

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

    3 nights from Fri 28th Nov $647

    Secure your holiday with a 30% deposit* Book now
  • A white house with a peaked roof a black front door and paving in front at Lobster Lookout in Swanage
    42
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fantastic three-bedroom house resting in Swanage, Dorset. (Ref. 1102492)

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

    3 nights from Sat 29th Nov $1045

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a wooden gate and a sign reading Salisbury Terrace surrounded by a garden at Jasmine Cottage in Kilmington Devon
    17
    Kilmington, Devon, Devon
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A traditional, pet-friendly, semi-detached cottage nestled in Kilmington, Devon. (Ref. 1096104)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 7th Dec $390

    Secure your holiday with a 30% deposit* Book now
  • Stone terraced houses with red doors and red leafy trees behind wooden fences
    18
    Swanage, Dorset
    • 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 $582

    Secure your holiday with a 30% deposit* Book now
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