Winter Short Breaks in Dorset

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Your search returned 474 cottages.

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  • A balcony with a table and two chairs overlooking a harbor with boats and buildings at Harbourside Penthouse in Brewers Quay Harbour
    21
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A contemporary and spacious third floor apartment on the Old Harbourside in Weymouth. (Ref. 999829)

    • Wi-fi
    • Off-road parking

    3 nights from Sat 29th Nov €733

    Secure your holiday with a 30% deposit* Book now
  • A waterfront with boats and buildings including Buccaneer Cottage at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Pretty cottage in the heart of Weymouth. (Ref. 994047)

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

    3 nights from Sat 29th Nov €848

    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 €496

    Secure your holiday with a 30% deposit* Book now
  • Stone cottage with thatched roof and white door along a narrow road at Wayside Stoke Abbot near Beaminster
    23
    Stoke Abbot near Beaminster, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      3.9★

      Good

    • Dream Cottages rating

    Wayside is a charming, two-bedroom cottage residing in Stoke Abbot near Beaminster, Dorset. (Ref. 1138149)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov €468

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a stone house with wooden windows and door on a gravel ground at The Stables Burton Bradstock
    31
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property located in peaceful village of Burton Bradstock. (Ref. 1069215)

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

    3 nights from Sat 29th Nov €801

    Secure your holiday with a 30% deposit*
    Last booked today
    Book now
  • A living room with an orange armchair green sofa and ottoman wooden bookcase and hanging plants at Harbour Retreat in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. (Ref. 1139963)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov €623

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
    20
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    3 nights from Fri 28th Nov €694

    Secure your holiday with a 30% deposit* Book now
  • A single story house with a tiled roof a chimney and an antenna on a lawn at Broadstones in Bridport
    37
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A pleasant, detached bungalow resting in Bettiscombe outside Bridport, Dorset. (Ref. 1105472)

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

    3 nights from Fri 28th Nov €615

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a thatched roof and blue front door on a street at Cornflower Cottage Burton Bradstock
    36
    Burton Bradstock, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    This picture-perfect, Grade II listed thatched cottage sits in Burton Bradstock, Dorset. (Ref. 1092014)

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

    3 nights from Sat 29th Nov €845

    Secure your holiday with a 30% deposit* Book now
  • A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
    17
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    3 nights from Fri 28th Nov €848

    Secure your holiday with a 30% deposit* Book now
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