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 brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
    56
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • Pet FriendlyNo

      5.0★

      Perfect

    • Dream Cottages rating

    The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. (Ref. 1059621)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Games room

    7 nights from Sun 6th Jun From €2249

    Book now
  • An outdoor area with a house, plants, and pathway at Brookfield Lodge in Drimpton
    42
    Drimpton, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Wheelchair friendly holiday cottage. (Ref. 967289)

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

    7 nights from Sat 21st Aug From €659

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  • An outdoor patio with a table and chairs in front of a stone cottage with large windows and a glass door at Puffin Cottage in Hawkchurch
    21
    Hawkchurch, Devon
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Romantic single storey cottage in Hawkchurch. (Ref. 1020961)

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

    7 nights from Fri 4th Jun From €892

    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
    • Pet FriendlyYes

      5.0★

      Perfect

    • Dream Cottages rating

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

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

    7 nights from Sat 10th Jul From €1859

    Book now
  • A white brick building with green framed windows a red post box a stone statue of a dog a garden with flowers and a red bicycle at Old Post Office Sherborne
    Property has offers
    46
    Sherborne, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      5.0★

      Perfect

    • Dream Cottages rating

    Old Post Office is a contemporary, four-bedroom home resting rurally in Glanvilles Wootton near Sherborne, Dorset. (Ref. 1129395)

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

    • 5% off - Tue 8th Sep to 31st Oct 2026

    7 nights from Fri 4th Jun From €2670

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  • A house with a brick exterior and driveway at The Chocolate Box in Weymouth
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

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

    7 nights from Sat 5th Jun From €1672

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  • A house facade with a door and bench at Cozy Cottage in Poole
    26
    Poole, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Poole Quay Cottage is a welcoming, mid-terrace holiday cottage with private parking that rests in Poole, Dorset, just a short distance from the coast. (Ref. 1192690)

    • Wi-fi
    • Off-road parking

    7 nights from Sat 28th Aug From €1061

    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 4th Jun From €771

    Book now
  • A row of attached houses with multiple windows and doors along a street at Quay Cottage Sea View in Poole
    33
    Poole, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Quay Cottage is an opulent, three-storey property resting in the seaside town of Poole, Dorset. (Ref. 1136862)

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

    7 nights from Fri 11th Jun From €1256

    Book now
  • A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
    46
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fabulous three-bedroom holiday home in Wyke Regis, Dorset. (Ref. 1103441)

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

    7 nights from Fri 4th Jun From €1322

    Book now
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