Winter Short Breaks in Dorset

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Your search returned 472 cottages.

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  • A row of terraced houses on a street with paved sidewalk and cobblestone road at Lobster Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    Lovely and comfortable cottage next to the harbour in Weymouth. (Ref. 994351)

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

    3 nights from Fri 28th Nov €562

    Secure your holiday with a 30% deposit* Book now
  • 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 29th Nov €557

    Secure your holiday with a 30% deposit* Book now
  • Stone house exterior with green door and windows surrounded by plants and small trees at Fiddlesticks Cottage in Beaminster
    25
    Beaminster, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    This detached, 19th century cottage rests in Beaminster, Devon. (Ref. 1120154)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov €549

    Secure your holiday with a 30% deposit* Book now
  • A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    3 nights from Fri 28th Nov €592

    Secure your holiday with a 30% deposit* Book now
  • A brick house with six windows and a central door with plants on the pavement at Manor Farm House in Bere Regis
    43
    Bere Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Manor Farm House is a charming Georgian abode with two woodburning stoves and accepting pets, located in the picturesque village of Bere Regis, Dorset. (Ref. 1158581)

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

    3 nights from Sat 29th Nov €650

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  • A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth
    36
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. (Ref. 1164179)

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

    3 nights from Sat 29th Nov €492

    Secure your holiday with a 30% deposit* Book now
  • A single story wooden house with gray roof a blue bench outside at Beside the Sea in Eype
    24
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming two-bedroom chalet resting on Eypes Mouth Chalet Park in Eype, Dorset. (Ref. 1089040)

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

    3 nights from Fri 28th Nov €714

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  • An outdoor patio with a wooden table and chairs an umbrella fruit basket and ocean view at Seacliff in West Bay
    32
    West Bay, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      3.8★

      Good

    • Dream Cottages rating

    High quality accommodation located in one of Dorset’s popular areas of West Bay. (Ref. 994629)

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

    3 nights from Fri 28th Nov €966

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A cottage with a thatched roof brick walls and a wooden door surrounded by grass at Cosy Cot in Stapleford
    20
    Stapleford, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Utterly Idyllic thatched cottage with the 'wow' factor in stunning village. (Ref. 988969)

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

    3 nights from Sat 29th Nov €804

    Secure your holiday with a 30% deposit* Book now
  • Modern apartment buildings with balconies behind trees under a clear sky at Flat 7 Sand Acres in Canford Cliffs
    29
    Canford Cliffs, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Flat 7 Sand Acres is an impressive apartment in Canford Cliffs, Dorset, that is close to the beach with amazing seaside views from the 26-foot balcony. (Ref. 1172882)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov €549

    Secure your holiday with a 30% deposit* Book now
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