Dorset Holiday Cottages for 2026

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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
  • 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
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

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

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

    7 nights from £465

    Last booked 2 days ago
    Book now
  • A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
    45
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. (Ref. 1107011)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £485

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  • An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
    38
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. (Ref. 1137640)

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

    7 nights from £665

    Book now
  • A brick barn with black door and large windows and a bench outside at Meadow View Barn in Bere Regis
    29
    Bere Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, modern barn located in the Dorset village of Bere Regis. (Ref. 1000906)

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

    7 nights from £500

    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
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

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

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

    7 nights from £461

    Book now
  • A small stone patio with a round table and chairs next to a wooden bench outside a stone house at Tiddlers Cottage in Uploders near Bridport
    45
    Uploders near Bridport, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. (Ref. 1117867)

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

    7 nights from £408

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

      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 £1364

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  • A single-story building with white walls and wooden framed windows and door surrounded by gravel and shrubs at Russet in Martin
    24
    Martin, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Lovely semi-detached barn in rural Hampshire. (Ref. 988894)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from £466

    Book now
  • An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
    33
    Ringstead, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    This quirky, converted bunker rests in Ringstead near Preston, Dorset. (Ref. 1131689)

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

    7 nights from £864

    Last booked yesterday
    Book now
  • A sitting area with two sofas and a dining table with chairs overlooking the sea at Sandpiper Chalet in Eype
    28
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming single-storey holiday home nestled in the quaint village of Eype, Dorset. (Ref. 1078226)

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

    7 nights from £537

    Book now
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