Winter Short Breaks in Dorset

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Your search returned 456 cottages.

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

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

    3 nights from Sun 11th Jan €630

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

      5.0

      Perfect

    • Dream Cottages rating

    Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. (Ref. 1156408)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 17th Jan was €645 €569

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    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A delightful, single-storey home resting in Stockland near Honiton, Devon. (Ref. 1131012)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • 5% off - Wed 7th Jan to 31st Jan 2026

    3 nights from Mon 12th Jan €691

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

      4.6

      Outstanding

    • Dream Cottages rating

    A well-presented, ground-floor apartment in Weymouth, Dorset. (Ref. 1126298)

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

    3 nights from Fri 16th Jan was €501 €418

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Upper ground floor apartment in the Admiral’s Quarter development. (Ref. 994438)

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

    3 nights from Sun 11th Jan €572

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    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.9

      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 Fri 13th Feb €814

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    3 nights from Sat 21st Feb €843

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    3 nights from Sun 22nd Feb €707

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A well-positioned, three-storey property resting in Weymouth, Dorset. (Ref. 1118939)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 11th Jan €779

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    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    A lovely ground-floor maisonette apartment resting in Boscombe, Dorset. (Ref. 1086302)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Fri 27th Mar to 9th Apr 2026

    3 nights from Sun 25th Jan €557

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