Winter Short Breaks in Dorset

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Your search returned 490 cottages.

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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 $631

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Stylish and contemporary cottage in the heart of Corfe Castle, Dorset. (Ref. 994182)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 28th Nov $742

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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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
    • 5% off - Tue 13th May to 13th Jun 2025

    3 nights from Sat 29th Nov $597

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 29th Nov $827

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

      4.4

      Good

    • Dream Cottages rating

    A period conversion apartment Bayview Loft is located in an upmarket development in a highly desirable area of Weymouth in Dorset. (Ref. 1085793)

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

    3 nights from Fri 28th Nov $668

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • 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

    3 nights from Sat 29th Nov $747

    Secure your holiday with a 30% deposit* Book now
    • Sleeps10
    • Bedrooms5
    • PetsYes
    • 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 29th Nov $1500

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. (Ref. 1137374)

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

    3 nights from Sat 29th Nov $1336

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

      4.8

      Outstanding

    • Dream Cottages rating

    This quirky, converted bunker rests in Ringstead near Preston, Dorset. (Ref. 1131689)

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

    3 nights from Tue 6th Jan $1165

    Secure your holiday with a 30% deposit*
    Last booked 6 hours ago
    Book now
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    2-minute walk to Sandsfoot beach and the South West Coast path. (Ref. 994582)

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

    3 nights from Sat 29th Nov $905

    Secure your holiday with a 30% deposit* Book now
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  • Price (lowest first)
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