Holiday Cottages for October Half term

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Your search returned 431 cottages.

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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

    Book now
  • A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
    Property has offers
    46
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Elegant end of terrace Georgian Townhouse located in Weymouth. (Ref. 1071940)

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

    3 nights from Fri 30th Oct was £1235 £1180

    Book now
  • Sunny Croft - 977681 - photo 1
    28
    Broadmayne near Dorchester, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sunny Croft is a delightful 1930s bungalow in Broadmayne, near Dorchester, Dorset. (Ref. 977681)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Sun 25th Oct £734

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  • A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth
    24
    Greenhill Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    This plush, two-storey property is located in the Greenhill suburb of Weymouth, Dorset. (Ref. 1093991)

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

    3 nights from Fri 23rd Oct £559

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  • A street view of terraced houses with one painted blue and windows and doors visible at Mackerel Cottage in Weymouth
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. (Ref. 1141828)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 24th Oct £512

    Last booked 2 days ago
    Book now
  • A stone cottage with two light blue doors and white framed windows with flowers outside at Dormouse Cottage in Burton Bradstock
    34
    Burton Bradstock, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A traditional, thatched cottage nestled in Burton Bradstock, close to Dorset's Jurassic Coast. (Ref. 1135014)

    • Wi-fi
    • Washing machine

    3 nights from Sun 25th Oct £478

    Book now
  • A coastal area with a golf course a road and a residential neighborhood at Bayview Cottage in Southbourne
    24
    Southbourne, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A well-positioned, three-bedroom cottage resting in Southbourne, Dorset. (Ref. 1165067)

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

    3 nights from Sun 25th Oct £695

    Last booked yesterday
    Book now
  • A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
    Property has offers
    25
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A delightful, one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1133982)

    • Wi-fi
    • Dishwasher

    • 10% off - Fri 10th Apr to 23rd Apr 2026

    3 nights from Fri 30th Oct £612

    Book now
  • A brick barn with black door and large windows and a bench outside at Meadow View Barn in Bere Regis
    Property has offers
    29
    Bere Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Charming, modern barn located in the Dorset village of Bere Regis. (Ref. 1000906)

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

    • 20% off - Fri 3rd Apr to 17th Apr 2026

    3 nights from Fri 30th Oct was £554 £471

    Book now
  • An apartment building with multiple floors at Flat 13, Chesil House in Bridport
    33
    West Bay, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      3.8★

      Good

    • Dream Cottages rating

    Beachcombers, 13 Chesil House, a neat first-floor apartment in West Bay, Dorset, boasting beach views, and is near the pub, river, harbour and shop. (Ref. 1174085)

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

    3 nights from Sun 25th Oct £405

    Book now
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