Winter Short Breaks in Dorset

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Your search returned 477 cottages.

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  • A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
    Property has offers
    29
    Preston, Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    3 nights from Fri 19th Dec €683

    Secure your holiday with a 30% deposit* Book now
  • A two story house with chimneys surrounded by a garden with grass bushes and small trees at West Ridge in Boscombe
    65
    Boscombe, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A substantial, detached property built in the 1900s, situated in the Boscombe region near Bournemouth. (Ref. 923145)

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

    3 nights from Sat 29th Nov €815

    Secure your holiday with a 30% deposit* Book now
  • A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    3 nights from Fri 28th Nov €719

    Secure your holiday with a 30% deposit* Book now
  • A house with red roof and red door behind grassy hill with trees at Rempstone Farmhouse in Corfe Castle
    29
    Corfe Castle, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Rempstone Farmhouse, a delightful, detached holiday home resting near Corfe Castle in Dorset. (Ref. 1155019)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Washing machine
    • Games room

    3 nights from Mon 1st Dec €1036

    Secure your holiday with a 30% deposit* Book now
  • 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 7th Dec €569

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  • A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
    24
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Fri 28th Nov €665

    Secure your holiday with a 30% deposit* Book now
  • A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
    Property has offers
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

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

    3 nights from Fri 28th Nov was €579 €503

    Secure your holiday with a 30% deposit* 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 Fri 28th Nov €665

    Secure your holiday with a 30% deposit* Book now
  • A stone house exterior with green door and lattice windows surrounded by garden at The Old School House in Piddletrenthide
    32
    Piddletrenthide, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    An attractive, converted Victorian school resting within Piddletrenthide. (Ref. 933650)

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

    3 nights from Fri 28th Nov €608

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a brick building with multiple doors and windows and potted plants on gravel at The Apple Shed in Motcombe
    23
    Motcombe, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A homely cottage situated near the village of Motcombe, Dorset. (Ref. 957189)

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

    3 nights from Sat 3rd Jan €514

    Secure your holiday with a 30% deposit* Book now
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