Winter Short Breaks in Dorset

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Your search returned 489 cottages.

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  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov £420

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  • A house with a deck and outdoor furniture at Mallows Byre in Yetminster
    53
    Yetminster, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Mallows Byre is a delightful barn conversion situated in the historic village of Yetminster in Dorset with an outstanding freestanding bath and Smart TV. (Ref. 955342)

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

    3 nights from Mon 30th Nov £457

    Last booked yesterday
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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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  • 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

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  • An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour
    28
    Brewers Quay Harbour, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Four bedrooms in Kellaway Court, Weymouth. (Ref. 994219)

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

    3 nights from Wed 6th Jan £839

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  • A brick house with a tiled roof and white doors and windows surrounded by a garden with plants and shrubs at Thorncroft in West Bay
    29
    West Bay, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming chalet-style bungalow resting within the town of West Bay. (Ref. 1013337)

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

    3 nights from Sat 28th Nov £740

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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 living room with a TV cabinet, armchair, ottoman, fireplace, and dining table with chairs at Quarrier's Rest in Swanage
    32
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday home rests in Swanage, Dorset. (Ref. 1124578)

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

    3 nights from Thu 3rd Dec £572

    Last booked yesterday
    Book now
  • Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
    39
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This pretty, detached cottage lies in Preston, Dorset. (Ref. 1119018)

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

    3 nights from Sat 28th Nov £624

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  • 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

      4.7★

      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 Wed 6th Jan £460

    Book now
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