May Half-Term Breaks

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  • A garden with tables and chairs at Beck House in Weymouth
    New property
    28
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. (Ref. 1201741)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 7th May From $664

    Book now
  • An outdoor entrance with opened doors leading to a room at The Orchard in Ringstead
    New property
    31
    Ringstead, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

    • Dream Cottages rating

    The Orchard is a charming holiday hut in Ringstead, Dorset, featuring external sleeping huts, private garden space and pet‑friendly accommodation. (Ref. 1199396)

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

    3 nights from Fri 7th May From $795

    Book now
  • Stone house with wooden door and four windows and plants in front at Norden House in Maiden Newton
    29
    Maiden Newton, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A character filled property resting in the pretty village of Maiden Netwon in Dorset. (Ref. 1072294)

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

    3 nights from Fri 30th Apr From $1044

    Book now
  • A small bay with several boats on the water a sandy beach and people near the shore with bushes and flower pots in the foreground at Beach View House in Wyke Regis
    28
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. (Ref. 1091445)

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

    3 nights from Sun 2nd May From $968

    Last booked 2 days ago
    Book now
  • A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Fri 30th Apr From $861

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  • A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
    31
    Preston, Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    3 nights from Fri 30th Apr From $832

    Last booked yesterday
    Book now
  • The exterior of a modern house with curved walls dark framed windows a paved pathway and garden beds at Flat 2 38 Preston Road Weymouth
    27
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1037083)

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

    3 nights from Fri 30th Apr From $663

    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

    3 nights from Sun 2nd May From $730

    Book now
  • A house with a garden and patio furniture at The Coach House near Charminster
    32
    Near Charminster, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

    • Dream Cottages rating

    The Coach House is an appealing detached holiday home near Charminster, Dorset, featuring a balcony and enclosed lawn. (Ref. 1199783)

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

    3 nights from Fri 30th Apr From $617

    Book now
  • A long brick and flint building with multiple doors and windows a grass lawn and flowers at The Old Stables in Winterborne Stickland
    39
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Fri 7th May From $831

    Book now
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