Winter Short Breaks in Dorset

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Your search returned 489 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    This sweet semi-detached dairy conversion rests in the village of Cucklington in Somerset. (Ref. 1021740)

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

    3 nights from Sat 28th Nov £476

    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.1

      Good

    • Dream Cottages rating

    A charming thatched roof character cottage resting in the village of Osmington, Dorset. (Ref. 1064960)

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

    3 nights from Sat 28th Nov £494

    Last booked yesterday
    Book now
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    3 nights from Sat 28th Nov £1157

    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

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

    3 nights from Sat 28th Nov £459

    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    Anchor Cottage is a traditional 19th-century Portland Stone cottage resting in the charming village of Weston, Portland, Dorset, with off-road parking. (Ref. 1160217)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Sat 28th Nov £476

    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Luxury coastal ground floor property, located on Fishermans Bank, Mudeford. (Ref. 1006623)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • 20% off - Wed 23rd Dec 2026 to 5th Jan 2027

    3 nights from Sun 29th Nov £707

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2

      Good

    • Dream Cottages rating

    Happiness Cottage is a character cottage with a contemporary style, woodburning stove and enclosed garden resting in the village of Piddlehinton in Dorset. (Ref. 1175141)

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

    3 nights from Sat 28th Nov £483

    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      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 28th Nov £739

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Sandy Haven is a delightful, ground-floor apartment resting in Swanage, Dorset. (Ref. 1140492)

    • Wi-fi
    • Ground floor bedroom

    3 nights from Sat 28th Nov £554

    Last booked yesterday
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. (Ref. 1129331)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov £581

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