Winter Short Breaks in Dorset

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Your search returned 326 cottages.

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  • A stone cottage with a thatched roof and blue front door on a street at Cornflower Cottage Burton Bradstock
    36
    Burton Bradstock, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    This picture-perfect, Grade II listed thatched cottage sits in Burton Bradstock, Dorset. (Ref. 1092014)

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

    3 nights from Sun 1st Mar £731

    Book now
  • A living room with sofas a coffee table a fireplace a television and wall art at Victorian Town House in Weymouth
    36
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms5
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. (Ref. 1035186)

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

    3 nights from Sun 1st Mar £652

    Last booked yesterday
    Book now
  • A semi detached house with a driveway and potted plants at The Anchorage in Bournemouth
    38
    Bournemouth, Dorset
    • Sleeps6
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A bright, ground-floor apartment resting in the lively seaside town of Bournemouth, Dorset. (Ref. 1128806)

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

    3 nights from Sun 1st Mar £619

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  • A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth
    24
    Greenhill Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    This plush, two-storey property is located in the Greenhill suburb of Weymouth, Dorset. (Ref. 1093991)

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

    3 nights from Sun 1st Mar £559

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  • A stone and brick house with arched windows a green door a bench and gravel driveway at The Coach House at Lackington Farm in Piddletrenthide
    57
    Piddletrenthide, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Gold Gems Award Winner for Best on the South Coast 2023. (Ref. 1087048)

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

    3 nights from Sun 1st Mar £689

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  • A street view of terraced houses with one painted blue and windows and doors visible at Mackerel Cottage in Weymouth
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. (Ref. 1141828)

    • Wi-fi
    • Dishwasher

    3 nights from Mon 2nd Mar £512

    Last booked yesterday
    Book now
  • A stone cottage with a thatched roof and a wooden table and benches outside at Magnolia Cottage Osmington
    41
    Osmington, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    Magnolia cottage is situated in Osmington. (Ref. 994367)

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

    3 nights from Sun 1st Mar £608

    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
    • PetsNo

      4.9★

      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 Sun 1st Mar £651

    Last booked yesterday
    Book now
  • A single story house with a tiled roof a chimney and an antenna on a lawn at Broadstones in Bridport
    37
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pleasant, detached bungalow resting in Bettiscombe outside Bridport, Dorset. (Ref. 1105472)

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

    3 nights from Sun 1st Mar £533

    Book now
  • A brick house with black doors and windows a bench and potted plants outside at Meadow View Barn in Bere Regis
    Property has offers
    29
    Bere Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, modern barn located in the Dorset village of Bere Regis. (Ref. 1000906)

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

    • 10% off - Fri 3rd Apr to 17th Apr 2026

    3 nights from Fri 6th Mar was £594 £471

    Book now
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