Winter Short Breaks in Dorset

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Your search returned 453 cottages.

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  • Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
    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 Wed 21st Jan $826

    Secure your holiday with a 30% deposit* 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
    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 Sat 17th Jan $594

    Secure your holiday with a 30% deposit* Book now
  • The Old Post Office - 1127439 - photo 1
    Property has offers
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. (Ref. 1127439)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 17th Jan $699

    Secure your holiday with a 30% deposit* Book now
  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    Property has offers
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 13th Feb $568

    Secure your holiday with a 30% deposit* Book now
  • A living room with two blue sofas a wooden coffee table a rug a TV a bookshelf and a fireplace at Ammonite Cottage Fortuneswell Portland
    Property has offers
    32
    Fortuneswell Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Traditional Portland Cottage. (Ref. 993922)

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

    3 nights from Sat 14th Feb $715

    Secure your holiday with a 30% deposit* Book now
  • A carport with gravel driveway and trees at The Halt in Maiden Newton
    Property has offers
    31
    Maiden Newton, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. (Ref. 1165359)

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

    • 10% off - Sat 3rd Jan to 31st Jan 2026

    3 nights from Thu 29th Jan $423

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • The front exterior of a red brick house with white framed windows and a white front door at 74 Reap Lane Southwell near Weston
    30
    Southwell near Weston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. (Ref. 1158199)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 17th Jan $625

    Secure your holiday with a 30% deposit* Book now
  • A white brick exterior of two adjacent houses with black and green doors and windows at Wey Cottage in Weymouth
    Property has offers
    17
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Traditional terraced cottage, 3 minutes' walk to the harbour, shop and café. (Ref. 998260)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 17th Jan $607

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
    35
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

    • Wi-fi
    • Off-road parking
    • Baby-friendly

    3 nights from Sat 17th Jan $610

    Secure your holiday with a 30% deposit* Book now
  • An outdoor patio area with a table umbrella and chairs in front of a building with brown doors and windows at Little Barn in Cucklington near Wincanton
    15
    Cucklington near Wincanton, Somerset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Rural semi-detached dairy conversion. (Ref. 1021741)

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

    3 nights from Sat 17th Jan $552

    Secure your holiday with a 30% deposit* Book now
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