Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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  • An outdoor area with a table and umbrella at Corner Barn in Winterborne Stickland
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sat 28th Nov £393

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  • 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 Sat 28th Nov £457

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  • A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
    41
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1092449)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov £493

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  • 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

      4.9★

      Outstanding

    • 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 30th Nov £921

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  • A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
    85
    Weymouth, Dorset
    • Sleeps18
    • Bedrooms9
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. (Ref. 1123341)

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

    3 nights from Mon 30th Nov £2610

    Last booked yesterday
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  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    24
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    3 nights from Sat 5th Dec £576

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  • Exterior of a single story stone and brick cottage with black windows and doors and two flower pots at Keepers Cottage in Winterborne Stickland
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sat 28th Nov £400

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  • A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
    49
    Weymouth, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

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

    3 nights from Sat 28th Nov £1025

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  • A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
    56
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. (Ref. 1059621)

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

    3 nights from Sat 28th Nov £918

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  • A small bay with several boats on the water a sandy beach and people near the shore with bushes and flower pots in the foreground at Beach View House in Wyke Regis
    28
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. (Ref. 1091445)

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

    3 nights from Sat 28th Nov £717

    Last booked yesterday
    Book now
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