Winter Short Breaks in Dorset

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Your search returned 472 cottages.

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

      4.1★

      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 29th Nov $566

    Secure your holiday with a 30% deposit* Book now
  • Stone terraced houses with red doors and red leafy trees behind wooden fences
    18
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sea Breeze is a lovely, terraced cottage resting in the outskirts of Swanage, Dorset. (Ref. 1150773)

    • Wi-fi
    • Off-road parking

    3 nights from Mon 1st Dec $570

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A stone and brick house with arched windows a green door a bench and gravel driveway at The Coach House at Lackington Farm in Piddletrenthide
    57
    Piddletrenthide, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Gold Gems Award Winner for Best on the South Coast 2023. (Ref. 1087048)

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

    3 nights from Fri 28th Nov $820

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A stone cottage with a thatched roof and white windows beside a road at Little Berwick Cottage in Burton Bradstock
    23
    Burton Bradstock, Dorset
    • Sleeps8
    • Bedrooms5
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    Full of Character thatched cottage just outside Burton Bradstock. (Ref. 994004)

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

    3 nights from Sat 29th Nov $850

    Secure your holiday with a 30% deposit* Book now
  • A modern residential area with brick and stone buildings a driveway and a streetlamp at Sea Gem in Castletown Portland
    43
    Castletown, Portland, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    3 nights from Fri 28th Nov $1210

    Secure your holiday with a 30% deposit* Book now
  • A living room with sofas a patterned rug a TV and a fireplace at Brewers House in Weymouth
    38
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    A tasteful, three-storey Victorian terrace cottage in the popular Dorset resort of Weymouth. (Ref. 1002126)

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

    3 nights from Fri 28th Nov $1082

    Secure your holiday with a 30% deposit* Book now
  • A living room with teal sofas a wooden coffee table a television on a corner stand and a dining area with wooden chairs at Louisa Cottage Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Beautiful and spacious cottage over three floors in Weymouth. (Ref. 994354)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Fri 28th Nov $627

    Secure your holiday with a 30% deposit* Book now
  • A brick cottage with a paved driveway a wooden door and a small lawn at Frome Lodge House in Frome Whitfield
    22
    Frome Whitfield, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A charming, two-bedroom holiday home resting in Frome Whitfield, Dorset. (Ref. 1132783)

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

    3 nights from Fri 28th Nov $589

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A row of terraced houses on a street with paved sidewalk and cobblestone road at Lobster Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.3★

      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 Fri 28th Nov $641

    Secure your holiday with a 30% deposit* Book now
  • A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
    41
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1092449)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sat 29th Nov $636

    Secure your holiday with a 30% deposit* Book now
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