May Half-Term Breaks

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Your search returned 275 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    A well-appointed apartment resting in Weymouth, Dorset. (Ref. 1003082)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Wed 28th May £656

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

      4.8

      Outstanding

    • Dream Cottages rating

    A charming townhouse set over three floors in the centre of Dorchester. (Ref. 1077743)

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

    3 nights from Sun 25th May £826

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    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    3 nights from Sat 31st May was £990 £510

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    • Sleeps8
    • Bedrooms4
    • PetsNo
    • 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
    • Washing machine
    • 10% off - Fri 21st Feb to 30th Jun 2025

    3 nights from Sat 31st May was £1325 £837

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

    • Wi-fi
    • Washing machine

    3 nights from Sun 25th May £498

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
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    • 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 Mon 26th May £465

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    A quaint, white-washed cottage resting in Weymouth, Dorset. (Ref. 1113457)

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

    3 nights from Fri 23rd May was £905 £585

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    • 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 31st May was £1028 £893

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps3
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    8 Biddlecombe Orchard is a contemporary property resting in the town of Bridport, Dorset. (Ref. 1152418)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Tue 27th May £493

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    • 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

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