May Half-Term Breaks

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Your search returned 443 cottages.

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    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    3 nights from Sun 24th May $1203

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

      4.9

      Outstanding

    • Dream Cottages rating

    Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. (Ref. 1144645)

    • Wi-fi
    • Baby-friendly

    3 nights from Wed 27th May $743

    Secure your holiday with a 30% deposit* Book now
    • 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 $1612

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

      4.6

      Outstanding

    • Dream Cottages rating

    Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. (Ref. 1058438)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 26th May $815

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    This wave shaped lodge is architect designed and has incredible panoramic sea views from the decking. (Ref. 994765)

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

    3 nights from Tue 26th May $1276

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3

      Good

    • Dream Cottages rating

    Alice's Cottage is a characterful, thatched cottage situated in Burton Bradstock, Dorset. (Ref. 1144638)

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

    3 nights from Wed 27th May $801

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    • 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
    • $325 off - Sat 27th Dec 2025 to 3rd Jan 2026

    3 nights from Tue 26th May $1099

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. (Ref. 1158199)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 26th May $617

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Dream Cottages rating

    The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. (Ref. 1127439)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 26th May $690

    Secure your holiday with a 30% deposit* Book now
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

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

    3 nights from Sun 31st May $613

    Secure your holiday with a 30% deposit* Book now
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