Dorset Holiday Cottages

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Your search returned 103 cottages.

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  • A small wooden house with large windows a gravel path leading to it and outdoor dining furniture with a parasol on a patio at Swandown 3 Blackdown in Cricket St Thomas
    26
    Cricket St. Thomas, Somerset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    A superb two-bedroom lodge in Cricket St. Thomas in Somerset. (Ref. 1112725)

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

    7 nights from £784

    Secure your holiday with a 30% deposit* Book now
  • A wooden house with a gray slate roof and patio furniture in a garden at Bramshurst in Upwey near Weymouth
    32
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. (Ref. 932159)

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

    7 nights from £622

    Secure your holiday with a 30% deposit* Book now
  • The entrance door to a brick house named The Mill House with flowers and plants on either side at Mill House in Maiden Newton
    50
    Maiden Newton, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsYes

      3.8★

      Good

    • Helpful Holidays rating

    Stunning Grade II listed house, located in the Maiden Newton area of Dorchester. (Ref. 990015)

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

    7 nights from £1123

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

      4.4★

      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 £606

    Secure your holiday with a 30% deposit* Book now
  • A small stone house with ivy on the walls and a garden in front at The Reading Room in Hinton St George
    Property has offers
    29
    Hinton St George, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Helpful Holidays rating

    This brilliant detached cottage is well-situated in Hinton St George, Somerset. (Ref. 1082466)

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

    • 20% off - Sat 19th Jul to 2nd Aug 2025

    • 10% off - Sat 2nd Aug to 17th Aug 2025

    • 20% off - Sun 17th Aug to 31st Aug 2025

    7 nights from £486

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A yellow two-story cottage with white-framed windows and a small porch with a green door at St Margarets Cottage in Tatworth near Chard
    15
    Tatworth near Chard, Somerset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Helpful Holidays rating

    Delightful, semi-detached period cottage in the South Somerset village of Tatworth. (Ref. 925543)

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

    7 nights from £334

    Secure your holiday with a 30% deposit* Book now
  • The front entrance door and windows of a stone building with plants and flowers in front at Scrambles Cottage in Stoke-Sub-Hamdon Somerset
    21
    Stoke-Sub-Hamdon, Somerset, Somerset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Helpful Holidays rating

    A traditional character cottage in Stoke-sub-Hamdon, Somerset. (Ref. 1126559)

    • Wi-fi
    • Dishwasher
    • Baby-friendly

    7 nights from £419

    Secure your holiday with a 30% deposit* Book now
  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Helpful Holidays rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £410

    Secure your holiday with a 30% deposit* Book now
  • A wooden house with large windows and a small patio table set in a garden at Swandown 2 Blackdown Cricket St Thomas near Chard
    Property has offers
    26
    Cricket St.Thomas near Chard, Somerset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Helpful Holidays rating

    A stunning single-storey lodge resting in Cricket St. Thomas in Somerset. (Ref. 1118174)

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

    • £277 off - Fri 27th Jun to 4th Jul 2025

    7 nights from £784

    Secure your holiday with a 30% deposit* Book now
  • A wooden exterior building with multiple windows and a central door at The Milking Barn in Yeovil Somerset
    30
    Yeovil, Somerset, Somerset
    • Sleeps6
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Helpful Holidays rating

    A superb, detached barn conversion situated on the outskirts of Yeovil. (Ref. 982461)

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

    7 nights from £709

    Secure your holiday with a 30% deposit* Book now
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