Winter Short Breaks in Dorset

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Your search returned 330 cottages.

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  • An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour
    Property has offers
    28
    Brewers Quay Harbour, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Four bedrooms in Kellaway Court, Weymouth. (Ref. 994219)

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

    3 nights from Sat 28th Feb £851

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  • Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
    Property has offers
    36
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. (Ref. 1058438)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Feb £621

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  • A brick and white semi detached house with bay windows and potted plants outside at Anchor House Weymouth
    68
    Weymouth, Dorset
    • Sleeps15
    • Bedrooms6
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. (Ref. 1105510)

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

    3 nights from Sat 28th Feb £1357

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  • A brick house with a brown door and windows a driveway wooden benches and a garage at Chickerell House Weymouth
    32
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. (Ref. 1152691)

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

    3 nights from Mon 2nd Mar £609

    Last booked 2 days ago
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  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    Property has offers
    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 Sat 28th Feb £608

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  • A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
    Property has offers
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    3 nights from Sat 28th Feb was £462 £438

    Last booked 2 days ago
    Book now
  • A stone cottage with a path leading to the door and a grassy field with a tree and sea in the background at Washingpools in West Bexington
    Property has offers
    28
    West Bexington, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Cosy property located in the coastal village of West Bexington. (Ref. 994761)

    • Off-road parking
    • Ground floor bedroom
    • Washing machine

    3 nights from Fri 6th Mar £439

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  • A row of houses with white and blue walls and small gardens along a brick pathway at Little Tern Brewers Quay Harbour
    31
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. (Ref. 1084006)

    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Feb £621

    Last booked 7 hours ago
    Book now
  • A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    3 nights from Sun 1st Mar £504

    Last booked 2 days ago
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  • A row of terraced houses on a street with paved sidewalk and cobblestone road at Lobster Cottage Brewers Quay Harbour
    Property has offers
    30
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Lovely and comfortable cottage next to the harbour in Weymouth. (Ref. 994351)

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

    3 nights from Sat 28th Feb was £513 £497

    Book now
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