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 single story wooden house with gray roof a blue bench outside at Beside the Sea in Eype
    24
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming two-bedroom chalet resting on Eypes Mouth Chalet Park in Eype, Dorset. (Ref. 1089040)

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

    3 nights from Wed 6th Jan From €716

    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 Mon 4th Jan From €574

    Book now
  • A white house with a peaked roof a black front door and paving in front at Lobster Lookout in Swanage
    42
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A fantastic three-bedroom house resting in Swanage, Dorset. (Ref. 1102492)

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

    3 nights from Tue 5th Jan From €969

    Book now
  • A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
    17
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    3 nights from Sun 29th Nov From €857

    Last booked 2 hours ago
    Book now
  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    3 nights from Sun 29th Nov From €828

    Last booked yesterday
    Book now
  • An outdoor seating area with a table and two chairs outside a small stone building at The Studio in Shaftesbury
    24
    Shaftesbury, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    An eye-catching stone cottage resting on the outskirts of Shaftesbury, Dorset. (Ref. 1008394)

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

    3 nights from Sat 28th Nov From €423

    Book now
  • A house with windows and a garden at June Cottage in Wool
    35
    Wool, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    June Cottage is a lovely cottage situated on the outskirts of Wool in Dorset, allowing pets and is well-situated to nearby attractions and amenities. (Ref. 1181945)

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

    3 nights from Sat 28th Nov From €728

    Book now
  • Exterior view of a two-story house with wooden paneling a balcony and metal railing at 6 Inveravon in Christchurch
    31
    Christchurch, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.4★

      Good

    • Dream Cottages rating

    6 Inveravon is a charming holiday home near the beach in the waterside town of Christchurch in Dorset with an open-plan living space and welcoming pets. (Ref. 1162271)

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

    3 nights from Sat 28th Nov From €861

    Book now
  • A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.3★

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    3 nights from Sun 29th Nov From €568

    Book now
  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    3 nights from Sun 29th Nov From €700

    Book now
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