Winter Short Breaks in Dorset

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Your search returned 471 cottages.

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  • A view of rooftops with chimneys and a cliff by the sea at Seaview in Swanage
    58
    Swanage, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This all-ground-floor cottage rests in the charming seaside resort of Swanage on the Jurassic Coast of Dorset. (Ref. 1012027)

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

    3 nights from Tue 16th Dec $857

    Secure your holiday with a 30% deposit* Book now
  • A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
    42
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. (Ref. 1107011)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 15th Dec $582

    Secure your holiday with a 30% deposit* Book now
  • A house with garage and driveway at The Chocolate Box in Weymouth
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Mon 15th Dec $923

    Secure your holiday with a 30% deposit* Book now
  • A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
    Property has offers
    32
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)

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

    • 15% off - Fri 19th Dec to 26th Dec 2025

    • 15% off - Fri 26th Dec 2025 to 2nd Jan 2026

    3 nights from Mon 15th Dec $634

    Secure your holiday with a 30% deposit* Book now
  • A garden with a tree a flower bed and a wooden picnic table outside a two story house at Molly's Place in Boscombe
    34
    Boscombe, Dorset
    • 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

    3 nights from Mon 15th Dec $589

    Secure your holiday with a 30% deposit* Book now
  • A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock
    Property has offers
    17
    Burton Bradstock, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A brightly decorated property resting within the village of Burton Bradstock. (Ref. 1008498)

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

    3 nights from Sat 20th Dec $646

    Secure your holiday with a 30% deposit* Book now
  • Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
    42
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)

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

    3 nights from Mon 15th Dec $1136

    Secure your holiday with a 30% deposit* Book now
  • A modern two story house with parking spaces and cars in front at Mary Bowes Terrace in Southbourne
    30
    Southbourne, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment set in the seaside town of Southbourne. (Ref. 1125968)

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

    3 nights from Thu 18th Dec $509

    Secure your holiday with a 30% deposit* Book now
  • A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
    28
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A lodge sleeping four people, Bowleaze area of Weymouth. (Ref. 994500)

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

    3 nights from Mon 15th Dec $881

    Secure your holiday with a 30% deposit* Book now
  • A white house with a peaked roof a black front door and paving in front at Lobster Lookout in Swanage
    42
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fantastic three-bedroom house resting in Swanage, Dorset. (Ref. 1102492)

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

    3 nights from Tue 16th Dec $1079

    Secure your holiday with a 30% deposit* Book now
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