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 living room with a TV on a stand a coffee table with board games a clock on the wall and large windows showing a sea view at Beach View Apartment 3 in Greenhill
    19
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Directly on the seafront. (Ref. 993989)

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

    3 nights from Mon 4th Jan From €787

    Book now
  • A row of modern brick and beige townhouses with balconies and large windows behind a green hedge at Kiama in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A well-positioned, three-storey property resting in Weymouth, Dorset. (Ref. 1118939)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 28th Nov From €756

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  • A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere
    21
    Mere, Wiltshire
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      5.0★

      Perfect

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

    • Pet friendly (extra charges may apply)
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    3 nights from Wed 2nd Dec From €640

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  • A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
    49
    Weymouth, Dorset
    • Sleeps9
    • Bedrooms4
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

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

    3 nights from Sun 3rd Jan From €1159

    Last booked 2 days ago
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  • A brick two-story house with balconies and a hedge in front at Harbour Reach 6 in Weymouth
    24
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A wonderful apartment that sleeps up to three people resting in Weymouth, Dorset. (Ref. 1057385)

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

    3 nights from Sun 29th Nov From €453

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  • 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
    • Pet FriendlyNo

      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 From €645

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  • An outdoor hot tub next to a blue house with glass doors and a garden with grass and bushes at Fisherman's Cottage in Southwell
    25
    Southwell, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

    • Dream Cottages rating

    A historic, 18th-century cottage resting in Portland, Dorset. (Ref. 1122551)

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

    3 nights from Mon 4th Jan From €880

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  • A grassy outdoor area with wooden picnic benches and a building with a tiled roof and fenced patio at The Old Stables in Winterborne Stickland
    33
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sat 28th Nov From €532

    Book now
  • A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
    20
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    3 nights from Mon 4th Jan From €678

    Book now
  • Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
    32
    Wakeham, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

    • Wi-fi
    • Washing machine

    3 nights from Mon 4th Jan From €579

    Book now
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