Winter Short Breaks in Dorset

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    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published

    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.8

      Outstanding

    • Dream Cottages rating

    A beautifully presented property resting in the pretty village of Burton Bradstock. (Ref. 1069147)

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

    3 nights from Sun 3rd Jan From $1413

    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.8

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Beautiful seafront apartment within the popular resort of Weymouth in Dorset. (Ref. 1003083)

    • Wi-fi
    • Dishwasher

    3 nights from Mon 30th Nov From $685

    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      4.8

      Outstanding

    • Dream Cottages rating

    Unwind in this stylish countryside retreat with a private, screened hot tub, cosy woodburner, pool table and spacious enclosed garden. (Ref. 1070465)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Mon 7th Dec From $1430

    Last booked yesterday
    Book now
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.5

      Outstanding

    • Dream Cottages rating

    Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. (Ref. 1091449)

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

    3 nights from Mon 4th Jan From $707

    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      5.0

      Perfect

    • Dream Cottages rating

    Old Post Office is a contemporary, four-bedroom home resting rurally in Glanvilles Wootton near Sherborne, Dorset. (Ref. 1129395)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Tue 8th Sep to 31st Oct 2026

    3 nights from Sun 3rd Jan From $1629

    Last booked yesterday
    Book now
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.5

      Outstanding

    • Dream Cottages rating

    A delightful cottage situated next to Weymouth harbour in Dorset. (Ref. 1061726)

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

    3 nights from Sat 28th Nov From $1122

    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.7

      Outstanding

    • Dream Cottages rating

    Rose Cottage, a charming thatched cottage nestled in Osmington, within Dorset National Landscape, boasts a large garden and proximity to local amenities. (Ref. 1200211)

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

    3 nights from Sat 28th Nov From $964

    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7

      Outstanding

    • Dream Cottages rating

    A charming, two-bedroom, thatched cottage resting in Burton Bradstock, Dorset. (Ref. 1124979)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From $801

    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8

      Outstanding

    • Dream Cottages rating

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

    • Wi-fi
    • Dishwasher

    3 nights from Sun 31st Jan From $839

    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9

      Outstanding

    • Dream Cottages rating

    Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. (Ref. 1171904)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Sun 3rd Jan From $628

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