Dorset Family Holidays

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Your search returned 405 cottages.

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  • A single-story house with a garage and a lawn at Shipton Hill View in Shipton Gorge
    36
    Shipton Gorge, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Situated in a stunning loaction overlooking hills in Dorset. (Ref. 994654)

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

    7 nights from $1175

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    7 nights from $832

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. (Ref. 994201)

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

    7 nights from $849

    Secure your holiday with a 30% deposit* Book now
  • A driveway leading to a single-story brick house with a red door and a small front lawn at Sunny Haven in Preston
    26
    Preston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A lovely two-bedroom bungalow resting in Preston, Dorset. (Ref. 1106680)

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

    7 nights from $749

    Secure your holiday with a 30% deposit* 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
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Luxurious 5 star contemporary property. (Ref. 993982)

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

    7 nights from $4457

    Secure your holiday with a 30% deposit*
    Last booked 7 hours ago
    Book now
  • A two-story house with stone and brick exterior a paved driveway and flowering bushes at The Brewery in Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property just moments from Weymouth harbour and Netwon's Cove in Dorset. (Ref. 1056258)

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

    7 nights from $779

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A living room with a TV cabinet, armchair, ottoman, fireplace, and dining table with chairs at Quarrier's Rest in Swanage
    32
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday home rests in Swanage, Dorset. (Ref. 1124578)

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

    7 nights from $699

    Secure your holiday with a 30% deposit* Book now
  • A dining room with a table set for dinner at Otter Cottage in Weymouth
    New property
    23
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A boutique, period home moments from Weymouth's iconic harbour. (Ref. 1177943)

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

    7 nights from $892

    Secure your holiday with a 30% deposit* Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    29
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

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

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

    7 nights from $903

    Secure your holiday with a 30% deposit* Book now
  • A backyard with a green lawn a patio dining set with an umbrella and a house with large windows and a sloped roof at Kings Cottage - South in Broad Chalke
    52
    Broad Chalke, Wiltshire
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Exceptional, lovingly restored cottage in Wiltshire's beautiful Chalke Valley. (Ref. 988982)

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

    7 nights from $1445

    Secure your holiday with a 30% deposit* Book now
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