Winter Short Breaks in Dorset

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Your search returned 481 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    This cosy lodge on a peaceful15 acre site, is resting near village of Milton on Stour in Dorset. (Ref. 967741)

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

    3 nights from Sat 29th Nov £413

    Secure your holiday with a 30% deposit* Book now
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A traditional farmhouse on the cliff top in Burton Bradstock, close to Hive Beach and it’s renowned café, West Bay, Wifi. (Ref. 994095)

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

    3 nights from Sat 29th Nov £413

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    • 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 £693

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    • Sleeps6
    • Bedrooms3
    • PetsYes
    • Dream Cottages rating

    Honeypot Cottage is a conventional, three-storey cottage situated near Swanage Beach in Swanage, Dorset, boasting a Smart TV and enclosed courtyard. (Ref. 1164485)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 29th Nov £541

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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. (Ref. 1078324)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov £472

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. (Ref. 1084006)

    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov £578

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    • 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 29th Nov £447

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. (Ref. 994321)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Sat 31st May to 14th Jun 2025

    3 nights from Sun 30th Nov £396

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Lovely early Victorian style Grade II listed cottage set in Warmwell village. (Ref. 994760)

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

    3 nights from Sat 29th Nov £536

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    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Beautiful and spacious cottage over three floors in Weymouth. (Ref. 994354)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Fri 28th Nov £473

    Secure your holiday with a 30% deposit* Book now
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