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 stone house with diamond lattice windows and a green door surrounded by trees at Warmwell Lodge in Warmwell
    28
    Warmwell, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Lovely early Victorian style Grade II listed cottage set in Warmwell village. (Ref. 994760)

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

    3 nights from Sat 28th Nov From $770

    Book now
  • 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 Sat 28th Nov From $815

    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 Sun 29th Nov From $678

    Book now
  • A gravel driveway with potted plants leading to a group of brick and white cottages with trees around at Little Stables Cottage in Spetisbury
    30
    Spetisbury, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A delightful, converted stable nestled in a quiet location on a working farm in the village of Spetisbury, Dorset. (Ref. 1127126)

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

    3 nights from Fri 5th Mar From $800

    Book now
  • A house with a front door and gravel driveway at Coastguard Lookout in Wyke Regis
    43
    Wyke Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    Coastguard Lookout is a modern, reverse-level house near a beach in Wyke Regis, Dorset, with off-road parking, Juliet balcony, and underfloor heating. (Ref. 1169223)

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

    3 nights from Sat 28th Nov From $598

    Last booked 2 days ago
    Book now
  • A stone and brick cottage with a tiled roof and a small garden beside a road at Way's Forge in Piddlehinton
    24
    Piddlehinton, Dorset
    • Sleeps3
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. (Ref. 994768)

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

    3 nights from Sat 28th Nov From $678

    Last booked yesterday
    Book now
  • A living room with a staircase and a sofa at Harbourside in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.4★

      Good

    • Dream Cottages rating

    Harbourside is a charming, dog-friendly, Grade II listed house in Weymouth, Dorset, set over three stories, with open-plan living and a private courtyard. (Ref. 1172365)

    • Pets go free
    • Wi-fi
    • Washing machine

    3 nights from Sun 29th Nov From $497

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

    • 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)

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

    3 nights from Sun 29th Nov From $856

    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
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

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

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

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

    3 nights from Sat 28th Nov From $837

    Book now
  • A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • Pet FriendlyNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    3 nights from Sun 29th Nov From $699

    Book now
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