May Half-Term Breaks

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Your search returned 342 cottages.

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  • A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
    29
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    A well-presented, mid-terrace property resting within the village of Wyke Regis. (Ref. 1006910)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 26th May £677

    Book now
  • Two armchairs with striped cushions by bay windows overlooking a beach at Three @ No36 in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. (Ref. 1162204)

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

    3 nights from Mon 1st Jun £656

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  • A front view of a brick house with a white door and blue garage door and a palm tree in the garden at Milton House in Weymouth
    29
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    A homely, mid-terraced holiday property resting in Weymouth, Dorset. (Ref. 1116564)

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

    3 nights from Sat 30th May £604

    Last booked yesterday
    Book now
  • A row of terraced houses with a yellow door and garden path surrounded by plants and flowers at Bedford Terrace in Bridport
    27
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    A pleasant two-bedroom terraced property nestled in Bridport, Dorset. (Ref. 1057844)

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

    3 nights from Sat 30th May £624

    Book now
  • An outdoor patio area with a table umbrella and chairs in front of a building with brown doors and windows at Little Barn in Cucklington near Wincanton
    15
    Cucklington near Wincanton, Somerset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Rural semi-detached dairy conversion. (Ref. 1021741)

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

    3 nights from Wed 27th May £408

    Last booked yesterday
    Book now
  • A red brick residential building with multiple windows and a paved driveway near a tree at Flat 6 Thornlow Heights in Weymouth
    Property has offers
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    A well-appointed, first-floor apartment resting in Weymouth, Dorset. (Ref. 1123245)

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

    3 nights from Fri 29th May £492

    Last booked yesterday
    Book now
  • A marina with boats docked and buildings in the background at Harbourside Haven Apartment 2 in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. (Ref. 1059263)

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

    3 nights from Mon 1st Jun £829

    Last booked 9 hours ago
    Book now
  • The exterior of two adjacent multi-story houses one pink and one brick with gray doors and white trim at Flat 3 - Muddleford in Bournemouth
    17
    Bournemouth, Dorset
    • Sleeps4
    • Bedrooms1
    • PetsNo

    • Dream Cottages rating

    Flat 3 is a romantic first-floor apartment resting in the city of Bournemouth in Dorset. (Ref. 1158719)

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

    3 nights from Sun 31st May £322

    Last booked yesterday
    Book now
  • An outdoor patio with a hot tub sofa and a small fireplace outside a cottage at Pheasant Lodge in Wimborne Minster
    Property has offers
    41
    Wimborne Minster, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A lovely, detached holiday home based on the outskirts of Wimborne Minster, East Dorset. (Ref. 974603)

    • Wi-fi
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher

    • 10% off - Fri 17th Apr to 1st May 2026

    3 nights from Fri 29th May was £695 £669

    Last booked 6 hours ago
    Book now
  • A patio with a table and chairs set outside a house with open glass doors and a large plant at Park Mews Weymouth
    Property has offers
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. (Ref. 1054948)

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

    3 nights from Sat 23rd May £985

    Book now
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