Winter Short Breaks in Dorset

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  • A white house with a peaked roof a black front door and paving in front at Lobster Lookout in Swanage
    42
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A fantastic three-bedroom house resting in Swanage, Dorset. (Ref. 1102492)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    3 nights from Sun 3rd Jan From €969

    Book now
  • A mobile home with a deck and palm tree at Whistler in Wimborne
    16
    Oakley, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    Whistler, a stylish pet-friendly lodge situated near Oakley, Dorset, boasts a freestanding bath, and proximity to a pub and New Forest National Park. (Ref. 1183901)

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

    3 nights from Sat 28th Nov From €581

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  • Stone house exterior with green door and windows surrounded by plants and small trees at Fiddlesticks Cottage in Beaminster
    25
    Beaminster, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    This detached, 19th century cottage rests in Beaminster, Devon. (Ref. 1120154)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Thu 3rd Dec From €568

    Book now
  • A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
    18
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Traditional cute cottage, in the town centre side of Weymouth harbour. (Ref. 994240)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Wed 6th Jan From €574

    Book now
  • An aerial view of a large house surrounded by fields and trees at Milton Manor in Milton On Stour
    79
    Milton On Stour, Dorset
    • Sleeps33
    • Bedrooms14
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sat 28th Nov From €5877

    Last booked yesterday
    Book now
  • A small white building with a shingled roof and two small trees in pots on either side of the door at Roundham Cottage in West Bay
    15
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A warm and restful converted annex in West Bay, Dorset. (Ref. 1067413)

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

    3 nights from Sun 3rd Jan From €629

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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
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

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

    • Pets go free
    • Dishwasher
    • Washing machine

    3 nights from Sun 3rd Jan From €691

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  • A table with a bottle and glass on a patio at Grass Roots in
    18
    Henstridge near Stalbridge, Somerset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Grass Roots is an inviting holiday cabin in Henstridge near Stalbridge, offering a jacuzzi and enclosed decking. (Ref. 1196345)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Sat 28th Nov From €558

    Book now
  • Harbour Reach 7 - 1194446 - photo 1
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Harbour Reach 7, an agreeable second-floor apartment in the town of Weymouth, in Dorset, boasts proximity to the beach, shop and pub and West Dorset Heritage Coast. (Ref. 1194446)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 29th Nov From €649

    Book now
  • 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
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

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

    • Pets go free
    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From €865

    Last booked yesterday
    Book now
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