Winter Short Breaks in Dorset

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A patio with a table and chairs under an umbrella outside a house with a tiled roof and a garden area at Rosamond in Shipton Gorge
    26
    Shipton Gorge, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    This lovely property rests in the pretty village of Shipton Gorge, Dorset. (Ref. 1020427)

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

    3 nights from Sat 28th Nov €778

    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

      4.8★

      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 Sun 29th Nov €572

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  • A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
    11
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A well-presented, ground-floor apartment in Weymouth, Dorset. (Ref. 1126298)

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

    3 nights from Sat 28th Nov €531

    Book now
  • A house with a garage and plants in front at Millmead House Annex Portesham
    New property
    27
    Portesham, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

    • Dream Cottages rating

    Millmead House Annex is a welcoming holiday annex in Portesham, Dorset, featuring open‑plan living, a woodburning stove and an enclosed garden. (Ref. 1201417)

    • Wi-fi
    • Off-road parking

    3 nights from Sat 28th Nov €389

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  • A brick apartment building with balconies and parking at Brewery View in Weymouth
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Brewery View is a stylish, first-floor apartment near the beach in Weymouth, Dorset, with an open-plan living space, balcony, and designated parking. (Ref. 1189426)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov €521

    Last booked yesterday
    Book now
  • A brick house with a tiled roof and white doors and windows surrounded by a garden with plants and shrubs at Thorncroft in West Bay
    29
    West Bay, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming chalet-style bungalow resting within the town of West Bay. (Ref. 1013337)

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

    3 nights from Sat 28th Nov €851

    Last booked yesterday
    Book now
  • A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
    44
    Sutton Poyntz, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)

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

    3 nights from Sun 6th Dec €610

    Last booked yesterday
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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 €1180

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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 Sun 29th Nov €526

    Last booked 2 days ago
    Book now
  • A sitting area with two sofas and a dining table with chairs overlooking the sea at Sandpiper Chalet in Eype
    28
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming single-storey holiday home nestled in the quaint village of Eype, Dorset. (Ref. 1078226)

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

    3 nights from Mon 30th Nov €618

    Book now
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