Winter Short Breaks in Dorset

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • 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 28th Nov $662

    Book now
  • A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
    27
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)

    • Wi-fi
    • Swimming pool
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov $740

    Book now
  • A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    3 nights from Wed 6th Jan $1035

    Book now
  • A patio with a metal table and two chairs outside a building with white framed windows and a glass door at 1 Cowdea Farm in Bettiscombe near Beaminster and Bridport
    31
    Bettiscombe near Beaminster and Bridport, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

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

    3 nights from Sat 28th Nov $617

    Book now
  • 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 Sun 29th Nov $820

    Book now
  • An outdoor view of a building with a driveway at Frome View in Wool
    New property
    31
    Wool, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

    • Dream Cottages rating

    Frome View is a one-bedroom property in Wool, Dorset, and a well-proportioned retreat for couples, perfectly positioned for coast and countryside. (Ref. 1205243)

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

    3 nights from Sun 29th Nov $862

    Book now
  • A house with white facade and windows at NO 10 Fortuneswell
    New property
    34
    Fortuneswell, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    NO 10 is a fine, dog-friendly house situated in Fortuneswell, Dorset, featuring an electric fire, an enclosed courtyard, and easy access to the beach. (Ref. 1200066)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 28th Nov $819

    Book now
  • 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

      4.3★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    3 nights from Sun 29th Nov $589

    Last booked yesterday
    Book now
  • A wooden cabin with a balcony, outdoor seating, and a hot tub on a grassy area at Swan Lodge Castle Farm in Wedmore
    19
    Wedmore, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A high-quality, modern lodge sat on the outskirts of charming Wedmore in Somerset. (Ref. 983734)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    3 nights from Tue 1st Dec $979

    Book now
  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    Property has offers
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 30% off - Mon 18th May to 25th Sep 2026

    3 nights from Sat 28th Nov $843

    Book now
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