May Half-Term Breaks

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Your search returned 438 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A delightful, converted stable nestled in a quiet location on a working farm in the village of Spetisbury, Dorset. (Ref. 1127126)

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

    3 nights from Fri 22nd May was $904 $881

    Secure your holiday with a 30% deposit* Book now
    • Sleeps3
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Gold Gems Award Winner for Best on the South Coast 2023. (Ref. 1087048)

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

    3 nights from Sun 31st May $963

    Secure your holiday with a 30% deposit*
    Last booked within the hour
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    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • 5% off - Fri 7th Mar 2025 to 30th Apr 2026

    3 nights from Sun 31st May $6578

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1

      Good

    • Dream Cottages rating

    Happiness Cottage is a character cottage with a contemporary style, woodburning stove and enclosed garden resting in the village of Piddlehinton in Dorset. (Ref. 1175141)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • 10% off - Fri 24th Oct to 12th Dec 2025

    3 nights from Sun 31st May $636

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

      4.6

      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 $973

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    • 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 Tue 26th May $837

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

    • Wi-fi
    • Off-road parking
    • Baby-friendly

    3 nights from Sun 31st May $623

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

      4.8

      Outstanding

    • Dream Cottages rating

    This detached, 19th century cottage rests in Beaminster, Devon. (Ref. 1120154)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 31st May $640

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    Last booked yesterday
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    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    A modern studio apartment on the seafront on Weymouth, Dorset. (Ref. 1003545)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 26th May $558

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    3 nights from Tue 26th May $751

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
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