Winter Short Breaks in Dorset

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Your search returned 480 cottages.

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  • A pathway leading to a white house with a brown door surrounded by bushes and flowers at Lilliput in Shipton Gorge
    55
    Shipton Gorge, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Beautiful and cosy cottage located in a peaceful village of Shipton Gorge. (Ref. 994340)

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

    3 nights from Fri 28th Nov €684

    Secure your holiday with a 30% deposit* Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    3 nights from Fri 28th Nov €821

    Secure your holiday with a 30% deposit* Book now
  • A row of modern brick and beige townhouses with balconies and large windows behind a green hedge at Kiama in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A well-positioned, three-storey property resting in Weymouth, Dorset. (Ref. 1118939)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 28th Nov €509

    Secure your holiday with a 30% deposit* Book now
  • 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 Fri 28th Nov €618

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  • A restaurant building with outdoor seating at The Beach Condo in Weymouth
    New property
    46
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsNo

    • Dream Cottages rating

    The Beach Condo, a quaint duplex apartment over three floors, in the heart of Weymouth in Dorset features stunning sea vistas, and a nearby beach and pub. (Ref. 1176421)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 29th Nov €1049

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  • A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
    21
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. (Ref. 1144645)

    • Wi-fi
    • Baby-friendly

    3 nights from Sat 29th Nov €617

    Secure your holiday with a 30% deposit* Book now
  • A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
    20
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    3 nights from Fri 28th Nov €672

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  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    3 nights from Fri 28th Nov €708

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A house with ivy on one side a paved driveway and a porch with wooden furniture at Deer Leap House in Moreton
    82
    Moreton, Dorset
    • Sleeps15
    • Bedrooms7
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A spacious holiday home resting in Moreton, Dorset. (Ref. 1060785)

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

    3 nights from Tue 2nd Dec €1738

    Secure your holiday with a 30% deposit* Book now
  • A two-story house surrounded by trees and shrubs with a grass lawn in front at The Old Post Office Cottage in Wareham
    46
    Wareham, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    A delightful detached house, set in large gardens, that will evoke feelings of being in an Enid Blyton Story. (Ref. 994562)

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

    3 nights from Sun 30th Nov €1081

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