Winter Short Breaks in Dorset

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Your search returned 456 cottages.

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  • 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 Tue 13th 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 Tue 13th Jan $552

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with black framed windows and a black door on a brick paved street at Stable Cottage Colyton
    27
    Colyton, Devon
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A Grade II listed former stable located in Colyton, in Devon, near to the Jurassic coast and beautiful countryside. (Ref. 1059490)

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

    3 nights from Tue 13th Jan $540

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    3 nights from Fri 16th Jan $855

    Secure your holiday with a 30% deposit* Book now
  • A hallway with wooden flooring a staircase at the end and various pieces of furniture and decorations on the walls at West Ridge in Boscombe
    Property has offers
    62
    Boscombe, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A substantial, detached property built in the 1900s, situated in the Boscombe region near Bournemouth. (Ref. 923145)

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

    • 5% off - Mon 5th Jan to 31st Jan 2026

    3 nights from Thu 29th Jan $993

    Secure your holiday with a 30% deposit* Book now
  • An outdoor patio area with tables umbrellas chairs and potted plants in front of a single story building at Willow Barn in Cucklington near Wincanton
    15
    Cucklington near Wincanton, Somerset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This sweet semi-detached dairy conversion rests in the village of Cucklington in Somerset. (Ref. 1021740)

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

    3 nights from Tue 13th Jan $644

    Secure your holiday with a 30% deposit* Book now
  • A house with a wooden door and windows next to a garden and trees at Tokenhill Cottage in Piddletrenthide
    44
    Piddletrenthide, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This well-presented three-bedroom property resides in Piddletrenthide, Dorset. (Ref. 1130975)

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

    3 nights from Tue 13th Jan $1079

    Secure your holiday with a 30% deposit* 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

      4.4★

      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 Tue 13th Jan $672

    Secure your holiday with a 30% deposit* Book now
  • A waterfront with boats and buildings including Buccaneer Cottage at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Pretty cottage in the heart of Weymouth. (Ref. 994047)

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

    3 nights from Tue 13th Jan $1039

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A driveway leading to a single-story brick house with a red door and a small front lawn at Sunny Haven in Preston
    26
    Preston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A lovely two-bedroom bungalow resting in Preston, Dorset. (Ref. 1106680)

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

    3 nights from Tue 13th Jan $806

    Secure your holiday with a 30% deposit* Book now
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