May Half-Term Breaks

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Your search returned 271 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Bright contemporary property perfect groups of guests in the Isle of Portland. (Ref. 994754)

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

    3 nights from Sat 31st May €893

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

      4.2

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    3 nights from Sat 31st May was €938 €731

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

      4.5

      Outstanding

    • Dream Cottages rating

    The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. (Ref. 1149531)

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

    3 nights from Sun 25th May €582

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

      4.2

      Good

    • Dream Cottages rating

    A delightful, three bed property nestled in the heart of Weymouth, Dorset. (Ref. 1132346)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 31st May €517

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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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 Sat 31st May was €1279 €1107

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

      4.5

      Outstanding

    • Dream Cottages rating

    A second-floor apartment resting in Weymouth. (Ref. 1007302)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Tue 27th May €523

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. (Ref. 932157)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 20% off - Fri 1st Aug to 29th Aug 2025

    3 nights from Fri 30th May €1310

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms1
    • PetsNo
    • Dream Cottages rating

    Flat 4 is a second floor duplex apartment resting in the city of Bournemouth in Dorset. (Ref. 1158720)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Tue 29th Apr to 31st May 2025

    3 nights from Sat 31st May was €667 €398

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

      4.2

      Good

    • Dream Cottages rating

    A well-presented, single-storey cottage resting in the village of Langton Matravers, Dorset. (Ref. 1074436)

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

    3 nights from Sat 31st May €477

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. (Ref. 1093760)

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

    3 nights from Sat 31st May was €1009 €973

    Secure your holiday with a 30% deposit* Book now
Most relevant
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  • Price (lowest first)
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  • Sleeps (highest first)
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  • Location (A to Z)
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