Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. (Ref. 1140944)

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

    3 nights from Sun 29th Nov $763

    Last booked yesterday
    Book now
    • Sleeps24
    • Bedrooms8
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    A Grade II listed farm house, resting within the village of Butcombe. (Ref. 1002613)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Tue 5th Jan $3885

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Character cottage in the coastal village of Burton Bradstock, sleeping four. (Ref. 994332)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 10% off - Fri 3rd Apr to 1st May 2026

    3 nights from Sat 28th Nov $823

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Half Pint Cottage, a lovely, 250-year-old dwelling situated in the town of Beaminster in Dorset, with a pet-friendly policy and a short walk from a pub. (Ref. 1153238)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 28th Nov $577

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4

      Good

    • Dream Cottages rating

    A pretty, renovated terraced cottage, close to the old harbour and Brewers Quay in Weymouth. (Ref. 1043009)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 29th Nov $776

    • Sleeps15
    • Bedrooms7
    • PetsYes

      4.2

      Good

    • Dream Cottages rating

    A spacious holiday home resting in Moreton, Dorset. (Ref. 1060785)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Tue 5th Jan $1991

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    A single-storey chalet in a wonderful location on the Eype Holiday Park, Dorset. (Ref. 1134626)

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

    3 nights from Mon 30th Nov $605

    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Stanley House is an exceptional harbourside cottage located in the heart of Weymouth, Dorset. (Ref. 1138865)

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

    3 nights from Sat 28th Nov $1568

    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. (Ref. 1114655)

    • Wi-fi
    • Washing machine
    • 10% off - Wed 4th Mar to 30th Apr 2026

    3 nights from Sat 28th Nov $728

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. (Ref. 994377)

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

    3 nights from Sat 19th Dec $797

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