Winter Short Breaks in Dorset

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Your search returned 487 cottages.

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  • The driveway and entrance of a house with trees plants a small shed and a black cat at Nuthatch in Honiton
    13
    Honiton, Devon
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, single-storey home resting in Stockland near Honiton, Devon. (Ref. 1131012)

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

    3 nights from Sun 29th Nov $657

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  • 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 Sat 28th Nov $889

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  • A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
    Property has offers
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. (Ref. 1156408)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    • 10% off - Tue 21st Apr to 31st May 2026

    3 nights from Sun 29th Nov $659

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  • 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 Sun 29th Nov $800

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  • A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. (Ref. 1078324)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov $657

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  • A stone house with a thatched roof and a wooden fence around the property at Dairy Cottage in Abbotsbury
    67
    Abbotsbury, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Dairy Cottage is a delightful, three-bedroom thatched cottage resting on a working farm on the outskirts of Abbotsbury, Dorset. (Ref. 1123043)

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

    3 nights from Sat 28th Nov $710

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  • Exterior view of a white townhouse with blue doors and railings and stone columns at Hops House in Brewers Quay Harbour
    25
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. (Ref. 994277)

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

    3 nights from Sun 29th Nov $1038

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  • A brick house with a tiled roof and white doors and windows surrounded by a garden with plants and shrubs at Thorncroft in West Bay
    29
    West Bay, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming chalet-style bungalow resting within the town of West Bay. (Ref. 1013337)

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

    3 nights from Sat 28th Nov $987

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  • 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 Sun 29th Nov $978

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  • The front entrance of a building with a dark door numbered 38 and a curved window with plants along the path at Flat 2 38 Preston Road Weymouth
    29
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1037083)

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

    3 nights from Sun 29th Nov $655

    Last booked yesterday
    Book now
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