May Half-Term Breaks

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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 house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    3 nights from Fri 30th Apr From $930

    Book now
  • The front entrance of a house with a green door and a window beside it with plants in black pots on a paved area at Sea Gem in Castletown Portland
    43
    Castletown, Portland, Dorset
    • Sleeps7
    • Bedrooms4
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    3 nights from Fri 30th Apr From $1210

    Book now
  • A house with a garden and pathway at 29 Bincleaves Road Weymouth
    New property
    55
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

    • Dream Cottages rating

    Coast Path Cottage is a delightful, pet-friendly house near a beach in Weymouth, Dorset, featuring a conservatory, enclosed garden, and off-road parking. (Ref. 1204253)

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

    3 nights from Sun 2nd May From $1051

    Book now
  • A small garden with a white metal table and chairs outside a brick house with white framed windows at Elm Villa in Wareham
    34
    Wareham, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A charming Victorian dwelling resting in the town of Wareham, Dorset. (Ref. 1053728)

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

    3 nights from Sun 2nd May From $768

    Book now
  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Wed 5th May From $968

    Book now
  • A row of colorful waterfront houses with windows and doors along a stone wall with wooden docks in front at Stanley House in Weymouth
    38
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      4.4★

      Good

    • Dream Cottages rating

    Stanley House is an exceptional harbourside cottage located in the heart of Weymouth, Dorset. (Ref. 1138865)

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

    3 nights from Fri 7th May From $1680

    Book now
  • A living room with a sofa armchair wooden chest coffee table dining table and plants at Beach Side in West Bay
    26
    West Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment resting in West Bay, Dorset. (Ref. 1095399)

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

    3 nights from Sat 1st May From $626

    Book now
  • A shopfront and residential buildings at Rope Cottage in Bridport
    37
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    Rope Cottage is a beautifully preserved Grade II listed former rope maker’s cottage in the heart of Bridport, Dorset, boasting a woodburning stove. (Ref. 1192255)

    • Wi-fi

    3 nights from Fri 30th Apr From $530

    Last booked yesterday
    Book now
  • A single story wooden house with gray roof a blue bench outside at Beside the Sea in Eype
    24
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming two-bedroom chalet resting on Eypes Mouth Chalet Park in Eype, Dorset. (Ref. 1089040)

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

    3 nights from Fri 30th Apr From $816

    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
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

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

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 4th May From $563

    Book now
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