Holiday Cottages for October Half term

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Your search returned 431 cottages.

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  • A house with garage and driveway at The Chocolate Box in Weymouth
    Property has offers
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

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

    3 nights from Fri 30th Oct was £971 £721

    Book now
  • A patio with a table and chairs under an umbrella outside a house with a tiled roof and a garden area at Rosamond in Shipton Gorge
    26
    Shipton Gorge, Dorset
    • 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 Sat 24th Oct £676

    Last booked 2 days ago
    Book now
  • A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
    29
    Preston, Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    3 nights from Sun 25th Oct £625

    Last booked 2 hours ago
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  • A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
    11
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A well-presented, ground-floor apartment in Weymouth, Dorset. (Ref. 1126298)

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

    3 nights from Sun 25th Oct £461

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  • A thatched roof cottage with white walls green bushes and a blue door at Lime Cottage in Burton Bradstock
    35
    Burton Bradstock, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A charming, two-bedroom, thatched cottage resting in Burton Bradstock, Dorset. (Ref. 1124979)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sat 24th Oct £598

    Book now
  • A waterfront with boats and buildings including Buccaneer Cottage at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Pretty cottage in the heart of Weymouth. (Ref. 994047)

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

    3 nights from Sat 24th Oct £776

    Book now
  • A wooden lodge with a deck and ramp on a grassy area at Manor Farm Lodge in Bowerchalke
    30
    Bowerchalke, Wiltshire
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This charming, two-bedroom holiday lodge rests in Bowerchalke, near Broad Chalke, Wiltshire. (Ref. 1111761)

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

    3 nights from Sat 24th Oct £564

    Last booked 5 hours ago
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  • A sitting area with two sofas and a dining table with chairs overlooking the sea at Sandpiper Chalet in Eype
    28
    Eype, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A charming single-storey holiday home nestled in the quaint village of Eype, Dorset. (Ref. 1078226)

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

    3 nights from Fri 23rd Oct £537

    Last booked yesterday
    Book now
  • A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
    43
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)

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

    3 nights from Wed 28th Oct £810

    Book now
  • A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
    41
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1092449)

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

    3 nights from Sat 24th Oct £493

    Book now
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