Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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  • 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

      4.7★

      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 Sun 29th Nov €657

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  • A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
    43
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)

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

    3 nights from Sat 28th Nov €923

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  • 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 28th Nov €889

    Last booked yesterday
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  • A stone house with a red tiled roof and glass doors surrounded by a garden and lawn at The Cosy Cowshed in Dalwood
    25
    Dalwood, Devon
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A beautiful and contemporary ground-floor dwelling set in the village of Dalwood, East Devon. (Ref. 1060217)

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

    3 nights from Sat 28th Nov €560

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  • An outdoor area with brick walls and pathways at The Cottage in Wimborne Minster
    44
    Wimborne Minster, Dorset
    • Sleeps6
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful single-storey holiday home resting in Wimborne Minster, Dorset. (Ref. 1111758)

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

    3 nights from Sat 28th Nov €511

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  • Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
    39
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This pretty, detached cottage lies in Preston, Dorset. (Ref. 1119018)

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

    3 nights from Sat 28th Nov €707

    Last booked yesterday
    Book now
  • An outdoor patio with a round wooden table and six chairs next to a garden and stone wall overlooking the sea at Beach View Apartment 2 in Greenhill
    35
    Greenhill, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Excellent period apartment in Weymouth close to the esplanade. (Ref. 993988)

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

    3 nights from Sun 29th Nov €1226

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  • Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
    32
    Wakeham, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

    • Wi-fi
    • Washing machine

    3 nights from Sun 29th Nov €588

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  • 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
    20
    Burton Bradstock, Dorset
    • 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 Sun 29th Nov €587

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  • A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth
    18
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Beautiful seafront apartment within the popular resort of Weymouth in Dorset. (Ref. 1003083)

    • Wi-fi
    • Dishwasher

    3 nights from Mon 30th Nov €579

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