Winter Short Breaks in Dorset

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Your search returned 489 cottages.

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  • An outdoor patio area with tables umbrellas chairs and potted plants in front of a single story building at Willow Barn in Cucklington near Wincanton
    15
    Cucklington near Wincanton, Somerset
    • 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

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  • Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington
    21
    Osmington, Dorset
    • 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
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • 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

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  • A patio with a metal table and two chairs outside a building with white framed windows and a glass door at 1 Cowdea Farm in Bettiscombe near Beaminster and Bridport
    31
    Bettiscombe near Beaminster and Bridport, Dorset
    • 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

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  • A stone house with windows and a garden with bushes in front at Anchor Cottage in Weston Portland
    35
    Weston, Portland, Dorset
    • 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

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  • A garden with a shed and a bench overlooking a body of water at Harbour View Mudeford in Christchurch
    Property has offers
    26
    Christchurch, Dorset
    • 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

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  • A cottage with a thatched roof and a garden at Happiness Cottage in Piddlehinton
    35
    Piddlehinton, Dorset
    • 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

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  • 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

      4.6★

      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

    Book now
  • An exterior view of a building with a door and windows and flower pots at the entrance at Sandy Haven in Swanage
    37
    Swanage, Dorset
    • 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
  • A garden with red roses and a metal chair beside a brick house at The Corner House in Weymouth
    39
    Weymouth, Dorset
    • 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

    Book now
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