May Half-Term Breaks

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Your search returned 456 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. (Ref. 1140944)

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

    3 nights from Sun 31st May $730

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Pets welcome. (Ref. 994050)

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

    3 nights from Sun 31st May $647

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4

      Good

    • Dream Cottages rating

    Pretty cottage in the heart of Weymouth. (Ref. 994047)

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

    3 nights from Sun 31st May $971

    Secure your holiday with a 30% deposit* Book now
    • Sleeps7
    • Bedrooms4
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

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

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    3 nights from Sun 31st May $1244

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Modern 3 Storey house. (Ref. 993939)

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

    3 nights from Sun 31st May $1030

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    A high-quality, modern lodge sat on the outskirts of charming Wedmore in Somerset. (Ref. 983734)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    3 nights from Sun 31st May $920

    Secure your holiday with a 30% deposit* Book now
    • Sleeps15
    • Bedrooms6
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. (Ref. 1105510)

    • Wi-fi
    • Off-road parking
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Sun 31st May $2346

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4

      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 $615

    Secure your holiday with a 30% deposit* Book now
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. (Ref. 1047698)

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

    3 nights from Fri 29th May $821

    Secure your holiday with a 30% deposit* Book now
    • 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 $784

    Secure your holiday with a 30% deposit* Book now
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