Holiday Cottages for October Half term

Your search returned 432 cottages.

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    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 10% off - Fri 19th Jun to 2nd Oct 2026

    3 nights from Sun 25th Oct £484

    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 25th Oct £608

    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A quaint stone-built cottage resting on the outskirts of Weymouth. (Ref. 1061544)

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

    3 nights from Fri 23rd Oct £574

    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    A superb cottage situated in the rural settlement of Farrington in Dorset. (Ref. 1003500)

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

    3 nights from Fri 30th Oct was £422 £349

    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • 10% off - Tue 5th May to 30th Jun 2026

    3 nights from Wed 28th Oct £470

    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sat 24th Oct £485

    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5

      Outstanding

    • Dream Cottages rating

    Sleeping 4 cosy cottage in Weymouth. (Ref. 994605)

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

    3 nights from Fri 23rd Oct £610

    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    This lovely property rests in the pretty village of Shipton Gorge, Dorset. (Ref. 1020427)

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

    3 nights from Sun 25th Oct £676

    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Dream Cottages rating

    Bubbs Cottage is a charming thatched cottage near Winfrith Newburgh, Dorset, boasting proximity to the Jurassic Coast, WiFi, a garden and allows pets. (Ref. 1183195)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 25th Oct £518

    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Miller’s Cottage is a snug and romantic dwelling located in the village of Puddletown, nearby a river in Dorset, with a woodburning stove and welcoming one pet. (Ref. 1160443)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 24th Oct £428

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