Summer Breaks in Dorset

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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
  • A building with balconies and stairs in front with a palm tree on the side at Lookout in Cove Castle
    Property has offers
    38
    Cove Castle, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Comfortable Spanish style holiday home in Weymouth. (Ref. 994352)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    • 15% off - Fri 14th Aug to 21st Aug 2026

    7 nights from Fri 14th Aug From $1794

    Book now
  • A house with a red tiled roof garage a tree with white flowers and green lawn at Bridge Studio in Broad Chalke
    39
    Near Broad Chalke, Wiltshire
    • Sleeps3
    • Bedrooms1
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Superb barn conversion in idyllic village, Stylishly furnished and with great space. (Ref. 988924)

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

    7 nights from Fri 28th Aug From $812

    Book now
  • A small white building with a shingled roof and two small trees in pots on either side of the door at Roundham Cottage in West Bay
    15
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A warm and restful converted annex in West Bay, Dorset. (Ref. 1067413)

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

    7 nights from Fri 21st Aug From $983

    Last booked yesterday
    Book now
  • A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. (Ref. 1078324)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from Fri 28th Aug From $1245

    Book now
  • The driveway and entrance of a house with trees plants a small shed and a black cat at Nuthatch in Honiton
    12
    Honiton, Devon
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, single-storey home resting in Stockland near Honiton, Devon. (Ref. 1131012)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub

    7 nights from Sat 22nd Aug From $1340

    Last booked yesterday
    Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    7 nights from Sat 29th Aug From $1757

    Book now
  • A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere
    21
    Mere, Wiltshire
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      5.0★

      Perfect

    • Dream Cottages rating

    Enchanting and unusual folly in an idyllic private setting. (Ref. 988942)

    • Pet friendly (extra charges may apply)
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    7 nights from Fri 31st Jul From $1252

    Book now
  • A building facade with windows and entrance at Number 3 by the Sea in Weymouth
    New property
    33
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

    • Dream Cottages rating

    Number 3 by the Sea is an inviting ground‑floor apartment located in Weymouth, Dorset, boasting sea views, a front patio and direct access to the beach. (Ref. 1203393)

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

    7 nights from Fri 28th Aug From $1027

    Last booked yesterday
    Book now
  • Front view of two adjoining houses with black doors and white brick walls with a paved driveway at Maisy Cottage in Weymouth
    25
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern and beautiful cottage in the heart of Weymouth. (Ref. 994369)

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

    7 nights from Sat 29th Aug From $909

    Book now
  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from Fri 28th Aug From $832

    Book now
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