Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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  • A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 28th Nov £647

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  • An exterior view of a stone house with wooden windows and door on a gravel ground at The Stables Burton Bradstock
    31
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property located in peaceful village of Burton Bradstock. (Ref. 1069215)

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

    3 nights from Sat 28th Nov £694

    Last booked 7 hours ago
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  • A stone cottage with a wooden gate and a sign reading Salisbury Terrace surrounded by a garden at Jasmine Cottage in Kilmington Devon
    17
    Kilmington, Devon, Devon
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A traditional, pet-friendly, semi-detached cottage nestled in Kilmington, Devon. (Ref. 1096104)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Wed 6th Jan £298

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  • A wooden cabin with a metal roof and green doors surrounded by a fenced patio with a picnic table and potted plants at Little Willow in Farrington near Child Okeford
    26
    Farrington near Child Okeford, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A superb cottage situated in the rural settlement of Farrington in Dorset. (Ref. 1003500)

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

    3 nights from Sat 28th Nov £349

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  • A stone cottage with black framed windows and a black door on a brick paved street at Stable Cottage Colyton
    27
    Colyton, Devon
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A Grade II listed former stable located in Colyton, in Devon, near to the Jurassic coast and beautiful countryside. (Ref. 1059490)

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

    3 nights from Sun 29th Nov £399

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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
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    3 nights from Sat 28th Nov £608

    Last booked 2 days ago
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  • A living room with a sofa armchair wooden chest coffee table dining table and plants at Beach Side in West Bay
    26
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment resting in West Bay, Dorset. (Ref. 1095399)

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

    3 nights from Sat 28th Nov £463

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  • A wooden deck with a picnic table set with glassware and fruit overlooking a grassy area and the sea at The Wave in Eype
    30
    Eype, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    This wave shaped lodge is architect designed and has incredible panoramic sea views from the decking. (Ref. 994765)

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

    3 nights from Sun 29th Nov £965

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  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    Property has offers
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 40% off - Fri 27th Feb to 25th Sep 2026

    3 nights from Sat 28th Nov £638

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  • A white semi detached house with blue doors and a blue fence under a clear sky at Ashwood Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern 3 Storey house. (Ref. 993939)

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

    3 nights from Sun 29th Nov £786

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