Winter Short Breaks in Dorset

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Your search returned 473 cottages.

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  • An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
    38
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. (Ref. 1137640)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine

    3 nights from Fri 28th Nov £642

    Secure your holiday with a 30% deposit* Book now
  • A single-story house with a garage and a lawn at Shipton Hill View in Shipton Gorge
    36
    Shipton Gorge, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a stunning loaction overlooking hills in Dorset. (Ref. 994654)

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

    3 nights from Sat 29th Nov £742

    Secure your holiday with a 30% deposit* Book now
  • Two adjacent houses with black front doors and small porches with awnings and shrubs outside at Anvil House in Brewers Quay Harbour
    25
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A pretty little modern house just a few minutes walk from the harbourside and local amenities. (Ref. 993929)

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

    3 nights from Fri 28th Nov £566

    Secure your holiday with a 30% deposit* Book now
  • A white brick exterior of two adjacent houses with black and green doors and windows at Wey Cottage in Weymouth
    17
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Traditional terraced cottage, 3 minutes' walk to the harbour, shop and café. (Ref. 998260)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 30th Nov £418

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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  • A house with a gravel driveway and plants at 32 Cranleigh Close in Tuckton
    45
    Tuckton, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A semi-detached dwelling situated within the quaint village of Tuckton, Bournemouth. (Ref. 997076)

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

    3 nights from Sat 29th Nov £541

    Secure your holiday with a 30% deposit* Book now
  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 29th Nov £472

    Secure your holiday with a 30% deposit* Book now
  • A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
    24
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Sleeps six in Weymouth, patio garden. (Ref. 994586)

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

    3 nights from Fri 28th Nov £641

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A dining table set with plates glasses and bread next to a living room with sofa armchairs coffee table and glass doors with green curtains at Newton's Cove View in Weymouth
    21
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Upper ground floor apartment in the Admiral’s Quarter development. (Ref. 994438)

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

    3 nights from Sat 29th Nov £484

    Secure your holiday with a 30% deposit* Book now
  • The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Ground Floor modern accommodation. (Ref. 994034)

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

    3 nights from Fri 28th Nov £445

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A house with a red tiled roof garage a tree with white flowers and green lawn at Bridge Studio in Broad Chalke
    35
    Broad Chalke, Wiltshire
    • Sleeps3
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Superb barn conversion in idyllic village, Stylishly furnished and with great space. (Ref. 988924)

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

    3 nights from Sat 29th Nov £452

    Secure your holiday with a 30% deposit* Book now
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