May Half-Term Breaks

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  • A stone house exterior with green door and lattice windows surrounded by garden at The Old School House in Piddletrenthide
    32
    Piddletrenthide, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An attractive, converted Victorian school resting within Piddletrenthide. (Ref. 933650)

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

    3 nights from Sun 31st May £556

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A window with binoculars on the sill looking out to buildings a clock tower and a marina at Anchorage View in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Anchorage View is a stunning, two-bedroom property resting in Weymouth, Dorset. (Ref. 1145912)

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

    3 nights from Tue 26th May £436

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
    18
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Traditional cute cottage, in the town centre side of Weymouth harbour. (Ref. 994240)

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

    3 nights from Sun 24th May £508

    Secure your holiday with a 30% deposit* Book now
  • A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. (Ref. 993976)

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

    3 nights from Sun 31st May £1209

    Secure your holiday with a 30% deposit* Book now
  • A hallway with wooden flooring a staircase at the end and various pieces of furniture and decorations on the walls at West Ridge in Boscombe
    62
    Boscombe, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A substantial, detached property built in the 1900s, situated in the Boscombe region near Bournemouth. (Ref. 923145)

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

    3 nights from Tue 26th May £734

    Secure your holiday with a 30% deposit* Book now
  • A driveway leading to a single-story brick house with a red door and a small front lawn at Sunny Haven in Preston
    26
    Preston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A lovely two-bedroom bungalow resting in Preston, Dorset. (Ref. 1106680)

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

    3 nights from Sun 24th May £606

    Secure your holiday with a 30% deposit* Book now
  • A white brick exterior of two adjacent houses with black and green doors and windows at Wey Cottage in Weymouth
    17
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Traditional terraced cottage, 3 minutes' walk to the harbour, shop and café. (Ref. 998260)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 31st May £449

    Secure your holiday with a 30% deposit* Book now
  • An old stone building with multiple gables and windows behind a stone wall at The Old Portland Courthouse in Portland
    33
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    The Old Portland Courthouse is spacious, comfortable luxury holiday home. (Ref. 994487)

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

    3 nights from Fri 22nd May £1209

    Secure your holiday with a 30% deposit* Book now
  • A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth
    36
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. (Ref. 1164179)

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

    3 nights from Tue 26th May £435

    Secure your holiday with a 30% deposit* Book now
  • A row of stone cottages with tiled roofs and painted doors on a sloped street at Pendennis in Sherborne
    17
    Sherborne, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Pendennis, a charming listed cottage in the heart of the beautiful town of Sherborne, Dorset. (Ref. 1148488)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Mon 1st Jun £406

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
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