May Half-Term Breaks

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Your search returned 342 cottages.

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    • Sleeps6
    • Bedrooms2
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    A bright, ground-floor apartment resting in the lively seaside town of Bournemouth, Dorset. (Ref. 1128806)

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

    3 nights from Sun 31st May £619

    • Sleeps6
    • Bedrooms1
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Beech is a well-presented safari tent resting in Stockland near Dalwood, Devon. (Ref. 1147768)

    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Baby-friendly

    3 nights from Mon 1st Jun £468

    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    30 Fleet Street is a lovely, pet-friendly two bedroom cottage located in the delightful town of Beaminster, Dorset and can sleep up to 5 guests. (Ref. 1161403)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Wed 27th May £477

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1

      Good

    • Dream Cottages rating

    Magnolia cottage is situated in Osmington. (Ref. 994367)

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

    3 nights from Mon 1st Jun £608

    Last booked 1 hour ago
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Charming, modern barn located in the Dorset village of Bere Regis. (Ref. 1000906)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • 20% off - Fri 3rd Apr to 17th Apr 2026

    3 nights from Fri 29th May was £596 £577

    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.2

      Good

    • 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 Tue 26th May £507

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. (Ref. 1058500)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 23rd May £1197

    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Old Harry Cottage is a delightful detached holiday home, with off-road parking, resting in the coastal town of Swanage in Dorset close to the beach. (Ref. 1162887)

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

    3 nights from Sun 31st May £664

    Last booked today
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    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8

      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 30th May £871

    Last booked today
    Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.0

      Good

    • Dream Cottages rating

    Mermaid Cottage is a delightful, contemporary cottage close to a beach and amenities, in the village of Wakeham, on the Isle of Portland, in Dorset. (Ref. 1143548)

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

    3 nights from Sun 31st May £489

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