Winter Short Breaks in Dorset

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Your search returned 487 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

    Last booked yesterday
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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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  • 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

    Last booked 2 days ago
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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

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  • A carport with gravel driveway and trees at The Halt in Maiden Newton
    Property has offers
    31
    Maiden Newton, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. (Ref. 1165359)

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

    • 10% off - Wed 20th May to 5th Jun 2026

    3 nights from Sat 28th Nov £312

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  • A pink house with open double doors and a picnic table on a grass lawn with a stone wall and countryside beyond at Cliff Farm No 2 Cottage Burton Bradstock
    23
    Burton Bradstock, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A traditional farmhouse on the cliff top in Burton Bradstock, close to Hive Beach and it’s renowned café, West Bay, Wifi. (Ref. 994095)

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

    3 nights from Sun 29th Nov £444

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  • The exterior entrance of a white building with potted plants and stone wall at The Town House in Dorchester
    42
    Dorchester, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A charming townhouse set over three floors in the centre of Dorchester. (Ref. 1077743)

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

    3 nights from Sun 29th Nov £849

    Last booked 2 days ago
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  • An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth
    16
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A cosy stone cottage for two this is the ideal place to spend quality time together, walking and exploring the local area. (Ref. 994208)

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

    3 nights from Sun 29th Nov £511

    Book now
  • A stone house with a brick extension and outdoor seating on a lawn with trees at Culverwells in Axminster
    32
    Axminster, Devon
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    In Dalwood village, East Devon. (Ref. 994151)

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

    3 nights from Tue 5th Jan £998

    Last booked 2 days ago
    Book now
  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    3 nights from Sun 29th Nov £608

    Last booked 2 days ago
    Book now
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