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
  • 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 $686

    Book now
  • An outdoor patio area with tables, chairs, and flower beds outside cream walls with blue doors and windows at The Compass in Swanage
    24
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Lovely apartment nestled in the thriving Dorest town of Swanage. (Ref. 979371)

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

    3 nights from Sun 29th Nov $494

    Book now
  • Stone cottage exterior with multiple windows a dark wooden door potted plants and a small tree at Tick Tock Cottage in Marnhull
    30
    Marnhull, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This fabulous Grade II listed cottage rests in the Dorset village of Marnhull. (Ref. 970616)

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

    3 nights from Mon 30th Nov $548

    Last booked yesterday
    Book now
  • 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 $597

    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

      4.7★

      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 $767

    Book now
  • A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
    42
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    3 nights from Sun 29th Nov $824

    Book now
  • Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
    42
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)

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

    3 nights from Wed 6th Jan $1202

    Book now
  • A house with a deck and outdoor furniture at Mallows Byre in Yetminster
    51
    Yetminster, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Mallows Byre is a delightful barn conversion situated in the historic village of Yetminster in Dorset with an outstanding freestanding bath and Smart TV. (Ref. 955342)

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

    3 nights from Mon 30th Nov $614

    Book now
  • A garden with a tree a flower bed and a wooden picnic table outside a two story house at Molly's Place in Boscombe
    34
    Boscombe, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A lovely ground-floor maisonette apartment resting in Boscombe, Dorset. (Ref. 1086302)

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

    3 nights from Wed 6th Jan $618

    Last booked 2 days ago
    Book now
  • The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
    26
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 29th Nov $711

    Book now
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