May Half-Term Breaks

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Your search returned 458 cottages.

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  • A thatched roof cottage with white walls green bushes and a blue door at Lime Cottage in Burton Bradstock
    35
    Burton Bradstock, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming, two-bedroom, thatched cottage resting in Burton Bradstock, Dorset. (Ref. 1124979)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 31st May £598

    Secure your holiday with a 30% deposit* Book now
  • A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
    50
    Weymouth, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

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

    3 nights from Sun 31st May £1025

    Secure your holiday with a 30% deposit* Book now
  • A two story house with chimneys surrounded by a garden with grass bushes and small trees 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 Sun 31st May £734

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a building with a door and windows and flower pots at the entrance at Sandy Haven in Swanage
    35
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Sandy Haven is a delightful, ground-floor apartment resting in Swanage, Dorset. (Ref. 1140492)

    • Wi-fi
    • Ground floor bedroom

    3 nights from Sun 31st May £499

    Secure your holiday with a 30% deposit* Book now
  • A gravel driveway and wooden gate in front of a brick and white house with plants and trees at Little Stables Cottage in Spetisbury
    Property has offers
    33
    Spetisbury, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A delightful, converted stable nestled in a quiet location on a working farm in the village of Spetisbury, Dorset. (Ref. 1127126)

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

    • 5% off - Fri 1st Aug to 31st Aug 2025

    3 nights from Mon 1st Jun £602

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a white townhouse with blue doors and railings and stone columns at Hops House in Brewers Quay Harbour
    25
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. (Ref. 994277)

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

    3 nights from Sun 24th May £1006

    Secure your holiday with a 30% deposit* Book now
  • A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. (Ref. 1156408)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 31st May £494

    Secure your holiday with a 30% deposit*
    Last booked today
    Book now
  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      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 Sun 24th May £657

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house with a double garage and driveway adjacent to trees at 1 Charlotte Close in Talbot Village Poole
    38
    Talbot Village, Poole, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A traditional four-bedroom cottage resting in Talbot Village, Dorset. (Ref. 1105314)

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

    3 nights from Sun 31st May £913

    Secure your holiday with a 30% deposit* Book now
  • A harbor with boats docked next to a row of buildings by the water at Monarch in Brewers Quay Harbour
    39
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      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 31st May £485

    Secure your holiday with a 30% deposit* Book now
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