Holiday Cottages for October Half term

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Your search returned 424 cottages.

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  • A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    3 nights from Sun 25th Oct £524

    Book now
  • A living room with sofas a coffee table a fireplace a television and wall art at Victorian Town House in Weymouth
    36
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms5
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. (Ref. 1035186)

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

    3 nights from Sat 24th Oct £652

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  • A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    3 nights from Wed 28th Oct £438

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  • A row of yellow terraced houses with street lamps and paved walkways at Olympic Cottage in Portland
    23
    Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern and spacious cottage for couples or family in the Isle of Portland. (Ref. 994497)

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

    3 nights from Fri 23rd Oct £638

    Last booked yesterday
    Book now
  • A front view of a house with windows and door at Guinea Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    Two bedroom cottage close to Weymouth harbour. (Ref. 994236)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 25th Oct £392

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  • 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 Sun 25th Oct £451

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  • A row of terraced houses on a street with paved sidewalk and cobblestone road at Lobster Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Lovely and comfortable cottage next to the harbour in Weymouth. (Ref. 994351)

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

    3 nights from Wed 28th Oct £497

    Last booked 9 hours ago
    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 Sun 25th Oct £408

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  • Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington
    21
    Osmington, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A charming thatched roof character cottage resting in the village of Osmington, Dorset. (Ref. 1064960)

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

    3 nights from Sun 25th Oct £494

    Last booked 2 days ago
    Book now
  • A stone building with white framed windows and a door along a paved street in a residential area at Brewers Retreat in Weymouth
    Property has offers
    22
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. (Ref. 1114655)

    • Wi-fi
    • Washing machine

    • 10% off - Wed 4th Mar to 30th Apr 2026

    3 nights from Sat 24th Oct £556

    Book now
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