Winter Short Breaks in Dorset

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Your search returned 489 cottages.

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  • A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
    27
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Sleeping 4 cosy cottage in Weymouth. (Ref. 994605)

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

    3 nights from Sat 16th Jan €700

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  • A stone pathway leads to a white house with a slate roof surrounded by trees and garden at Marles Farmhouse in Salwayash
    43
    Salwayash, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Beautiful converted farmhouse. (Ref. 976544)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Tue 5th Jan €1748

    Last booked 2 days ago
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  • A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. (Ref. 1091449)

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

    3 nights from Sun 29th Nov €617

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  • A balcony with two chairs a table with a bottle of champagne and glasses overlooking greenery and water at Waters Edge in Wyke Regis
    35
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern family house located on the edge of Weymouth, with sea views. (Ref. 994759)

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

    3 nights from Sun 29th Nov €775

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  • Stone cottage exterior with multiple windows a dark wooden door potted plants and a small tree at Tick Tock Cottage in Marnhull
    30
    Marnhull, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This fabulous Grade II listed cottage rests in the Dorset village of Marnhull. (Ref. 970616)

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

    3 nights from Mon 30th Nov €470

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  • A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. (Ref. 1133998)

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

    3 nights from Sat 28th Nov €610

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  • The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
    55
    Weymouth, Dorset
    • Sleeps13
    • Bedrooms6
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • Sky TV

    3 nights from Sat 28th Nov €1827

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  • A wooden lodge with a deck and ramp on a grassy area at Manor Farm Lodge in Bowerchalke
    30
    Bowerchalke, Wiltshire
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday lodge rests in Bowerchalke, near Broad Chalke, Wiltshire. (Ref. 1111761)

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

    3 nights from Sat 28th Nov €638

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  • A house with garage and driveway at The Chocolate Box in Weymouth
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

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

    3 nights from Sat 28th Nov €829

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  • A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
    44
    Sutton Poyntz, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)

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

    3 nights from Sun 6th Dec €610

    Book now
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