May Half-Term Breaks

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Your search returned 279 cottages.

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    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    A contemporary second-floor apartment resting on the Weymouth Seafront, Dorset. (Ref. 1092706)

    • Wi-fi
    • Dishwasher

    3 nights from Sun 25th May $760

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    The Cheesehouse is an exceptional, pet-friendly five-bedroom home resting in Litton Cheney, Dorset featuring a games room with pool, darts and bar area. (Ref. 1161994)

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

    3 nights from Sat 31st May was $1846 $1800

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

      4.8

      Outstanding

    • Dream Cottages rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    3 nights from Wed 28th May $608

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

      5.0

      Perfect

    • Dream Cottages rating

    This charming, two-bedroom holiday lodge rests in Bowerchalke, near Broad Chalke, Wiltshire. (Ref. 1111761)

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

    3 nights from Fri 30th May was $786 $714

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

      4.8

      Outstanding

    • Dream Cottages rating

    A delightful, ground-floor apartment set in the seaside town of Southbourne. (Ref. 1125968)

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

    3 nights from Tue 27th May $651

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

      4.7

      Outstanding

    • Dream Cottages rating

    Sea Breeze is a lovely, terraced cottage resting in the outskirts of Swanage, Dorset. (Ref. 1150773)

    • Wi-fi
    • Off-road parking

    3 nights from Fri 30th May was $777 $637

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

      5.0

      Perfect

    • Dream Cottages rating

    This fabulous Grade II listed cottage rests in the Dorset village of Marnhull. (Ref. 970616)

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

    3 nights from Mon 26th May $685

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

      4.9

      Outstanding

    • Dream Cottages rating

    A fantastic ground-floor apartment located in West Cliff near Bournemouth, Dorset. (Ref. 1083610)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • $462 off - Fri 1st Aug to 29th Aug 2025

    3 nights from Sat 31st May $1803

    Secure your holiday with a 30% deposit* Book now
    • Sleeps7
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. (Ref. 1091335)

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

    3 nights from Fri 23rd May was $1432 $1366

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

      4.7

      Outstanding

    • Dream Cottages rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • $69 off - Fri 9th May to 16th May 2025

    3 nights from Wed 28th May $594

    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)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
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  • Property name (Z to A)
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