Winter Short Breaks in Dorset

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Your search returned 494 cottages.

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    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • 5% off - Fri 7th Mar 2025 to 30th Apr 2026

    3 nights from Mon 1st Dec £4743

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

      4.7

      Outstanding

    • Dream Cottages rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • £52 off - Fri 9th May to 16th May 2025

    3 nights from Sun 30th Nov £352

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

      4.9

      Outstanding

    • Dream Cottages rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sun 30th Nov £402

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

      4.5

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    3 nights from Sat 29th Nov £487

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

      4.7

      Outstanding

    • Dream Cottages rating

    A delightful two-bedroom ground-floor apartment resting in Swanage, Dorset. (Ref. 1093320)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 10% off - Wed 23rd Apr to 12th Jun 2025

    3 nights from Sat 29th Nov £637

    Secure your holiday with a 30% deposit* Book now
    • Sleeps16
    • Bedrooms8
    • PetsYes
    • Dream Cottages rating

    Moles Cottage is a characterful retreat with en-suite bedrooms, a toasty open fire and accepting pets, in the picturesque village of Farnham, Dorset. (Ref. 1165807)

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

    3 nights from Sun 30th Nov £1767

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    • 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 29th Nov £486

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in a stunning loaction overlooking hills in Dorset. (Ref. 994654)

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

    3 nights from Sat 29th Nov £742

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. (Ref. 1097676)

    • Wi-fi

    3 nights from Sun 30th Nov £421

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

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    3 nights from Fri 28th Nov £566

    Secure your holiday with a 30% deposit* Book now
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