Winter Short Breaks in Dorset

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Your search returned 489 cottages.

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  • A thatched roof cottage with white walls green bushes and a blue door at Lime Cottage in Burton Bradstock
    35
    Burton Bradstock, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A charming, two-bedroom, thatched cottage resting in Burton Bradstock, Dorset. (Ref. 1124979)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov $784

    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 Wed 6th Jan $1193

    Last booked yesterday
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  • A carport with gravel driveway and trees at The Halt in Maiden Newton
    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

    3 nights from Sat 28th Nov $417

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  • An outdoor patio area with a glass table and six chairs under an umbrella next to a modern house at Bramley Cottage Henley near Langport
    41
    Henley near Langport, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    An exceptional detached property resting on the outskirts of Langport, Somerset. (Ref. 1074556)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Sky TV

    3 nights from Sun 29th Nov $1192

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  • 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 Sat 28th Nov $1109

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  • A modern two-story house with large triangular windows and a glass balcony railing at 5 Red Sails in Sandbanks
    50
    Sandbanks, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    5 Red Sails, a beautifully-presented home in the stunning neighbourhood of Sandbanks in Poole, Dorset. (Ref. 1151567)

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

    3 nights from Sun 29th Nov $1527

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  • A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere
    21
    Mere, Wiltshire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

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

    3 nights from Sat 28th Nov $730

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  • A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth
    27
    Nottington near Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A quaint stone-built cottage resting on the outskirts of Weymouth. (Ref. 1061544)

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

    3 nights from Mon 30th Nov $752

    Book now
  • A row of white and grey terraced houses with bushes and purple flowers in front at Bay Tree House in Seaton Devon
    61
    Seaton, Devon, Devon
    • Sleeps16
    • Bedrooms8
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A beautiful four-storey townhouse resting in the seaside town of Seaton, Devon. (Ref. 1063005)

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

    3 nights from Sat 28th Nov $2135

    Book now
  • A sitting area with two sofas and a dining table with chairs overlooking the sea at Sandpiper Chalet in Eype
    28
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming single-storey holiday home nestled in the quaint village of Eype, Dorset. (Ref. 1078226)

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

    3 nights from Mon 30th Nov $716

    Book now
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