Holiday Cottages for October Half term

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Your search returned 138 cottages.

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  • Front view of a brick terraced house with bay windows and a black front door at Pedaller's Cottage in Weymouth
    16
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Located in a quiet residential street in Weymouth, Pedaller’s cottage is a delightful home for families. (Ref. 994539)

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

    3 nights from Tue 28th Oct $1023

    Secure your holiday with a 30% deposit* Book now
  • A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    All second floor. (Ref. 994293)

    • Wi-fi

    3 nights from Tue 28th Oct $847

    Secure your holiday with a 30% deposit* Book now
  • A stone house with windows and a garden with bushes in front at Anchor Cottage in Weston Portland
    35
    Weston, Portland, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Anchor Cottage is a traditional 19th-century Portland Stone cottage resting in the charming village of Weston, Portland, Dorset, with off-road parking. (Ref. 1160217)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Wed 29th Oct $623

    Secure your holiday with a 30% deposit* Book now
  • A living room with a brown leather sofa blue armchair glass coffee table and television at Tides Corner in Bowleaze
    36
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A modern ground floor annex in Weymouth, just moments from the beach. (Ref. 994726)

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

    3 nights from Tue 28th Oct $1291

    Secure your holiday with a 30% deposit* Book now
  • Front entrance of Bay View Hotel with brick buildings and ivy on walls in Weymouth
    49
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    One @ No36 is a delightful duplex apartment with the beach on your doorstep, with the convenience of off-road parking, in Weymouth, Dorset. (Ref. 1162201)

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

    3 nights from Tue 28th Oct $827

    Secure your holiday with a 30% deposit* Book now
  • A living room with a blue armchair a colorful armchair a television a small fireplace and blue curtains at The Skipper's House in Weymouth
    36
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A delightful, three bed property nestled in the heart of Weymouth, Dorset. (Ref. 1132346)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Tue 28th Oct $590

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    An immaculate second-floor apartment resting in the centre of Weymouth. (Ref. 1059264)

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

    3 nights from Tue 28th Oct $1010

    Secure your holiday with a 30% deposit* Book now
  • A row of stone cottages with tiled roofs and painted doors on a sloped street at Pendennis in Sherborne
    17
    Sherborne, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Pendennis, a charming listed cottage in the heart of the beautiful town of Sherborne, Dorset. (Ref. 1148488)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Wed 29th Oct $535

    Secure your holiday with a 30% deposit* Book now
  • A dark wood cottage with a gravel driveway and potted plants at Belview Cottage Fifehead Neville near Sturminster Newton
    35
    Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A detached, modern cottage in the quiet hamlet of Fifehead Neville. (Ref. 1357)

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

    3 nights from Tue 28th Oct $551

    Secure your holiday with a 30% deposit* Book now
  • Modern apartment buildings with balconies behind trees under a clear sky at Flat 7 Sand Acres in Canford Cliffs
    29
    Canford Cliffs, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Flat 7 Sand Acres is an impressive apartment in Canford Cliffs, Dorset, that is close to the beach with amazing seaside views from the 26-foot balcony. (Ref. 1172882)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Thu 30th Oct $636

    Secure your holiday with a 30% deposit* Book now
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