Luxury Holiday Cottages 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 glass conservatory attached to a stone and tile roof building and wooden outdoor furniture on a patio at Fossil Barn in Weymouth
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Contemporary barn conversion, close to the Dorset coast. (Ref. 994207)

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

    7 nights from From $934

    Book now
  • A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
    59
    Osmington, Dorset
    • Sleeps12
    • Bedrooms5
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Luxurious 5 star contemporary property. (Ref. 993982)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from From $4688

    Last booked yesterday
    Book now
  • A gravel driveway in front of a building with large windows and a slate roof at The Courtyard - Hilltop Barn in Winterborne Zelston near Wareham
    41
    Winterborne Zelston near Wareham, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A beautiful detached barn conversion situated in the lovely Dorset area of Winterborne Zelston near Wareham and Wimborne Minster. (Ref. 1058078)

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

    7 nights from From $867

    Book now
  • Exterior of a single story stone and brick cottage with black windows and doors and two flower pots at Keepers Cottage in Winterborne Stickland
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

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

    7 nights from From $625

    Last booked yesterday
    Book now
  • A long brick and flint building with multiple doors and windows a grass lawn and flowers at The Old Stables in Winterborne Stickland
    39
    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

    7 nights from From $736

    Book now
  • A row of attached houses with multiple windows and doors along a street at Quay Cottage Sea View in Poole
    33
    Poole, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Quay Cottage is an opulent, three-storey property resting in the seaside town of Poole, Dorset. (Ref. 1136862)

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

    7 nights from From $1131

    Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    Property has offers
    24
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    • 5% off - Wed 1st Jul to 31st Aug 2026

    7 nights from From $854

    Book now
  • A living room with two black leather sofas, a wood-burning stove, a wooden coffee table, a floor lamp, a small TV on a wooden stand, and glass doors with orange curtains at The Old Cart Shed in Winterborne Stickland
    37
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Exceptional, spacious rural barn conversion. (Ref. 905897)

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

    7 nights from From $739

    Last booked yesterday
    Book now
  • An exterior view of a cottage with a wooden picnic table and umbrella on a paved patio at New Barn in Winterborne Stickland
    33
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Lovely, well-appointed single-storey cottage near Winterborne Stickland. (Ref. 905896)

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

    7 nights from From $619

    Book now
  • A stone cottage with a tiled roof and potted plants outside at Leys At Valley View Farm in Uplyme
    44
    Uplyme, Devon
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Leys at Valley View Farm is a high specification luxury barn conversion. (Ref. 994328)

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

    7 nights from From $1831

    Last booked yesterday
    Book now
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