Holiday Cottages for October Half term

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Your search returned 424 cottages.

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  • A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. (Ref. 993976)

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

    3 nights from Fri 30th Oct €1391

    Book now
  • A living room with a brown sectional sofa and decorative pillows a wooden coffee table with cups and a teapot two large windows with white shutters and a blue bean bag at Sunrise Apartment in Weymouth
    36
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. (Ref. 1097676)

    • Wi-fi

    3 nights from Wed 28th Oct €498

    Last booked yesterday
    Book now
  • An outdoor area with a wooden building and a small wooden cabin with a gravel ground and a wooden fence at Sunnyside Lodge in Crewkerne
    28
    Crewkerne, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Charming lodge situated near the Somerset market town of Crewkerne. (Ref. 976874)

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

    3 nights from Sun 25th Oct €653

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  • 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 Sun 25th Oct €883

    Last booked yesterday
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  • An old stone building with multiple gables and windows behind a stone wall at The Old Portland Courthouse in Portland
    33
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    The Old Portland Courthouse is spacious, comfortable luxury holiday home. (Ref. 994487)

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

    3 nights from Fri 23rd Oct €1391

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  • A narrow street with houses and a view of the water at Blanche Cottage Brewers Quay Harbour
    45
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A fabulous, three-storey home resting near Weymouth's Old Harbour in Dorset. (Ref. 1092575)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 25th Oct €799

    Last booked yesterday
    Book now
  • A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
    35
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

    • Wi-fi
    • Baby-friendly

    3 nights from Sun 25th Oct €519

    Last booked 5 hours ago
    Book now
  • A white cottage with a thatched roof and potted plants outside on a roadside at Amy Cottage in West Lulworth
    43
    West Lulworth, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Amy Cottage is a beautiful thatched cottage with a toasty gas fire and accepting pets, located in Dorset's West Lulworth on the Jurassic coastline. (Ref. 1166887)

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

    3 nights from Sun 25th Oct €841

    Book now
  • A patio with a metal table and two chairs outside a building with white framed windows and a glass door at 1 Cowdea Farm in Bettiscombe near Beaminster and Bridport
    Property has offers
    31
    Bettiscombe near Beaminster and Bridport, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

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

    • 5% off - Fri 6th Mar to 30th Apr 2026

    3 nights from Sun 25th Oct €529

    Last booked yesterday
    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 Fri 23rd Oct €758

    Book now
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