Dorset Holiday Cottages

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Your search returned 105 cottages.

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  • A garden with a grass lawn a wooden bench a patio table with chairs and a brick house in the background at Poppy Cottage in Charlton Marshall
    Property has offers
    21
    Charlton Marshall, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    Charming 19th century terraced cottage in handy village location. (Ref. 976077)

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

    • 5% off - Sat 18th Oct to 6th Dec 2025

    7 nights from $582

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • An exterior view of a stone house with wooden windows and a gate by a roadside at The Old Barn in Harman's Cross near Swanage
    29
    Harman's Cross near Swanage, Dorset
    • Sleeps10
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Helpful Holidays rating

    Impressive barn conversion in rural Dorset location, close to beaches and Corfe Castle. (Ref. 906024)

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

    7 nights from $946

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
    51
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Helpful Holidays rating

    Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. (Ref. 932158)

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

    7 nights from $784

    Secure your holiday with a 30% deposit* Book now
  • A stone building with wooden stairs leading to a balcony in a garden at Cherrywood Barn in South Petherton
    18
    South Petherton, Somerset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Pretty, detached stone built barn with lovely rural outlook. (Ref. 1052429)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from $485

    Secure your holiday with a 30% deposit* Book now
  • Stone cottages with plants in pots outside and a blue door at King Charles Cottage in Broadwindsor
    42
    Broadwindsor, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Helpful Holidays rating

    This is a mid-terrace cottage in the centre of Broadwindsor, Dorset. (Ref. 1006503)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $822

    Secure your holiday with a 30% deposit* Book now
  • An outdoor patio with wooden furniture and a white umbrella next to a wooden building surrounded by bushes at The Old Cart Shed in Rockbourne near Fordingbridge
    26
    Rockbourne near Fordingbridge, Hampshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Helpful Holidays rating

    Holiday cottage sleeping 6, close to New Forest. (Ref. 967949)

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

    7 nights from $768

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A small building with a red tiled roof white walls white double doors and climbing plants next to a gravel path and grass at Oke Apple Cottage in Okeford Fitzpaine
    11
    Okeford Fitzpaine, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Charming, detached single storey barn conversion. (Ref. 20119)

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

    7 nights from $453

    Secure your holiday with a 30% deposit* Book now
  • A house with outdoor seating area at Budmouth Upwey near Weymouth
    42
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Helpful Holidays rating

    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. (Ref. 932157)

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

    7 nights from $822

    Secure your holiday with a 30% deposit* Book now
  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Helpful Holidays rating

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. (Ref. 932160)

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

    7 nights from $920

    Secure your holiday with a 30% deposit* Book now
  • A wooden house with a large window wall and patio furniture on a lawn at Swandown 14 Goldenhaye Cricket St Thomas near Chard
    Property has offers
    25
    Cricket St. Thomas near Chard, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    A contemporary three-bedroom lodge resting in Cricket St. Thomas, near Chard in Somerset. (Ref. 1112209)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    • 10% off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from $1579

    Secure your holiday with a 30% deposit* Book now
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