May Half-Term Breaks

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Your search returned 452 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in a stunning loaction overlooking hills in Dorset. (Ref. 994654)

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

    3 nights from Sun 24th May £999

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    A charming chalet-style bungalow resting within the town of West Bay. (Ref. 1013337)

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

    3 nights from Sun 31st May £707

    Secure your holiday with a 30% deposit* Book now
    • 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 31st May £511

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps5
    • Bedrooms3
    • PetsNo
    • Dream Cottages rating

    Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. (Ref. 1047698)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • 10% off - Fri 6th Jun to 30th Jun 2025

    • 10% off - Mon 30th Jun to 31st Jul 2025

    3 nights from Fri 29th May £630

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

      4.8

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Sun 31st May £647

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

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    3 nights from Sun 31st May £504

    Secure your holiday with a 30% deposit*
    Last booked 6 hours ago
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. (Ref. 1137374)

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

    3 nights from Fri 29th May £1474

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A beautifully presented property located in peaceful village of Burton Bradstock. (Ref. 1069215)

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

    3 nights from Sun 31st May £827

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • 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 £1209

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Stylish and contemporary cottage in the heart of Corfe Castle, Dorset. (Ref. 994182)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 31st May £581

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