Dorset Holiday Cottages for 2026

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  • A wooden house with brick foundation surrounded by trees and plants at Willow Brook in Okeford Fitzpaine
    12
    Okeford Fitzpaine, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A well-presented barn conversion resting on the outskirts of Okeford Fitzpaine, Dorset. (Ref. 1137516)

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

    7 nights from £696

    Secure your holiday with a 30% deposit* Book now
  • Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
    42
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)

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

    7 nights from £860

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    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 £402

    Secure your holiday with a 30% deposit* Book now
  • A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
    46
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Elegant end of terrace Georgian Townhouse located in Weymouth. (Ref. 1071940)

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

    7 nights from £1180

    Secure your holiday with a 30% deposit* Book now
  • A coastal view with boats on water and a hill in the background at Portland Pebble in Wyke Regis
    43
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    An enticing, semi-detached house sitting in Wyke Regis, Dorset. (Ref. 1097679)

    • Wi-fi
    • Off-road parking

    7 nights from £702

    Secure your holiday with a 30% deposit* Book now
  • A modern two story house with parking spaces and cars in front at Mary Bowes Terrace in Southbourne
    30
    Southbourne, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment set in the seaside town of Southbourne. (Ref. 1125968)

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

    7 nights from £479

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A single story white building with a grey roof and glass entrance surrounded by a wooden fence at Cliff Barn in Burton Bradstock
    27
    Burton Bradstock, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A brightly decorated property resting within the village of Burton Bradstock, Dorset. (Ref. 1118787)

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

    7 nights from £483

    Secure your holiday with a 30% deposit* Book now
  • A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
    32
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)

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

    7 nights from £637

    Secure your holiday with a 30% deposit* Book now
  • A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
    28
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A lodge sleeping four people, Bowleaze area of Weymouth. (Ref. 994500)

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

    7 nights from £775

    Secure your holiday with a 30% deposit* Book now
  • A fenced swimming pool with chairs and lawn in front of a brick and wood house at Manor Farm Barn in Dewlish
    42
    Dewlish, Dorset
    • Sleeps15
    • Bedrooms8
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. (Ref. 1003646)

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

    7 nights from £2326

    Secure your holiday with a 30% deposit* Book now
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