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
  • A living room with two black leather sofas, a wood-burning stove, a wooden coffee table, a floor lamp, a small TV on a wooden stand, and glass doors with orange curtains at The Old Cart Shed in Winterborne Stickland
    37
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Exceptional, spacious rural barn conversion. (Ref. 905897)

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

    3 nights from Sat 28th Nov From £475

    Last booked 1 hour ago
    Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    3 nights from Sun 29th Nov From £733

    Book now
  • A cottage with a thatched roof and garden at The Elbow in Frampton
    45
    Frampton, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)

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

    3 nights from Sun 29th Nov From £482

    Last booked 2 days ago
    Book now
  • A street view with stone cottages and a thatched roof at Greenham Cottage in Norton-sub-Hamdon
    31
    Norton-sub-Hamdon, Somerset
    • Sleeps5
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A character property, resting within the delightful village of Norton-sub-Hamdon. (Ref. 1000796)

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

    3 nights from Sat 28th Nov From £499

    Last booked yesterday
    Book now
  • A long brick and flint building with multiple doors and windows a grass lawn and flowers at The Old Stables in Winterborne Stickland
    39
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Sat 28th Nov From £455

    Last booked 2 days ago
    Book now
  • An exterior view of a building with a door and windows and flower pots at the entrance at Sandy Haven in Swanage
    37
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      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 28th Nov From £554

    Book now
  • A garden with a hot tub and dining table at Mallow Cottage in Langton Matravers
    New property
    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 £651

    Book now
  • A row of modern brick and beige townhouses with balconies and large windows behind a green hedge at Kiama in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

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

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From £647

    Book now
  • A patio with a round table and two chairs with two mugs on the table overlooking a gravel area and green hills at Burton Bay in Burton Bradstock
    20
    Burton Bradstock, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Pets welcome. (Ref. 994050)

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

    3 nights from Sun 29th Nov From £510

    Book now
  • Front view of a two-storey house with white framed windows and doors with flowering bushes in front at Chine Heights in Bournemouth
    32
    Bournemouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A duplex apartment resting in the coastal town of Bournemouth, Dorset. (Ref. 1133748)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From £651

    Book now
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