May Half-Term Breaks

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Your search returned 304 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    This cosy lodge on a peaceful15 acre site, is resting near village of Milton on Stour in Dorset. (Ref. 967741)

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

    3 nights from Fri 30th May was £741 £482

    Secure your holiday with a 30% deposit* Book now
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 25th May £472

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

    3 nights from Sat 31st May was £766 £416

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

    23 Millhams Street, a stunning renovated Victorian cottage resting in the town of Christchurch in Dorset, close to a shop, a pub, and a beach. (Ref. 1162980)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Wed 28th May £626

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

      4.5

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 31st May was £793 £515

    Secure your holiday with a 30% deposit*
    Last booked 1 hour ago
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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2

      Good

    • Dream Cottages rating

    A well-presented, modern apartment on the rugged Isle of Portland. (Ref. 1034885)

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

    3 nights from Wed 28th May £504

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

      4.9

      Outstanding

    • Dream Cottages rating

    Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. (Ref. 994321)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Sat 31st May to 14th Jun 2025

    3 nights from Sat 31st May was £738 £405

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

    The Swanage Rail Lookout is a newly refurbished picturesque detached house boasting an enclosed garden, perfect for those with or without pets looking for a walking distance seaside holiday and/or train enthusiasts! (Ref. 1157056)

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

    3 nights from Fri 30th May was £943 £660

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

      4.4

      Good

    • 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 Fri 30th May £578

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)

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

    3 nights from Tue 27th May £520

    Secure your holiday with a 30% deposit* Book now
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