Winter Short Breaks in Dorset

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  • A small white building with a shingled roof and two small trees in pots on either side of the door at Roundham Cottage in West Bay
    15
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A warm and restful converted annex in West Bay, Dorset. (Ref. 1067413)

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

    3 nights from Sun 3rd Jan From $733

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  • A small dining area with a round glass table set for two and wicker chairs by two windows with ocean views at 6 The Beaches in Weymouth
    16
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.6★

      Outstanding

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

    A modern studio apartment on the seafront on Weymouth, Dorset. (Ref. 1003545)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From $567

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  • An outdoor area with brick walls and pathways at The Cottage in Wimborne Minster
    44
    Wimborne Minster, Dorset
    • Sleeps6
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful single-storey holiday home resting in Wimborne Minster, Dorset. (Ref. 1111758)

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

    3 nights from Sun 29th Nov From $701

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  • The front entrance of a house with a green door and a window beside it with plants in black pots on a paved area at Sea Gem in Castletown Portland
    43
    Castletown, Portland, Dorset
    • Sleeps7
    • Bedrooms4
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    3 nights from Mon 4th Jan From $1236

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  • A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
    23
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    3 nights from Sun 3rd Jan From $788

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  • A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      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 Fri 4th Dec From $670

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  • A garden with a stone table and chairs at Crantock
    36
    Sherborne, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

    • Dream Cottages rating

    Crantock is a welcoming, pet-friendly house in Sherborne, Dorset, featuring a garden patio with barbecue, private driveway parking, and a gas fire. (Ref. 1192425)

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

    3 nights from Sat 28th Nov From $1092

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  • A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.9★

      Outstanding

    • 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 Mon 4th Jan From $651

    Book now
  • A garden with a hot tub and dining table at Mallow Cottage in Langton Matravers
    47
    Langton Matravers, Dorset
    • Sleeps7
    • Bedrooms3
    • Pet FriendlyYes

    • Dream Cottages rating

    Mallow Cottage is a delightful cottage resting in the village of Langton Matravers, Dorset, with a hot tub, open-plan living, and parking. (Ref. 1176931)

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

    3 nights from Sat 28th Nov From $873

    Book now
  • A house with garage and driveway at The Chocolate Box in Weymouth
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From $968

    Last booked today
    Book now
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