Winter Short Breaks in Dorset

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Your search returned 489 cottages.

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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

    Last booked 2 days ago
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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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  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 28th Nov £485

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  • A large two-story house with multiple sliding glass doors and windows and outdoor seating on a grassy yard at Shutts House Garden Apartment in Coombe Bissett
    32
    Coombe Bissett, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Absolutely stunning, luxurious ground floor accommodation at the eastern end of Wiltshire's beautiful Chalke Valley. (Ref. 1016405)

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

    3 nights from Sat 28th Nov £1057

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  • A small bay with several boats on the water a sandy beach and people near the shore with bushes and flower pots in the foreground at Beach View House in Wyke Regis
    28
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. (Ref. 1091445)

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

    3 nights from Sat 28th Nov £717

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  • A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
    56
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. (Ref. 1059621)

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

    3 nights from Sat 28th Nov £918

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  • A garden with various plants and flowers outside a stone cottage with thatched roof at The Elbow in Frampton
    44
    Frampton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)

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

    3 nights from Sun 29th Nov £562

    Last booked yesterday
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  • A row of terraced houses with white and yellow facades and a sidewalk at Brewers Quay Harbour
    Property has offers
    28
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A delightful cottage situated next to Weymouth harbour in Dorset. (Ref. 1061726)

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

    3 nights from Sat 28th Nov £832

    Last booked yesterday
    Book now
  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    3 nights from Sun 29th Nov £650

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  • A large stone manor house with bay windows and ivy on the walls with a garden and small pond in front at Milton Manor in Milton On Stour
    82
    Milton On Stour, Dorset
    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sat 28th Nov £5028

    Book now
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