Holiday Cottages for October Half term

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Your search returned 441 cottages.

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  • A small A-frame house with a wooden deck and stairs surrounded by trees and grass at Apple Tree Lodge in Gillingham
    Property has offers
    23
    Gillingham, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Unique, A-frame lodge placed near Gillingham in Dorset. (Ref. 970181)

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

    3 nights from Fri 30th Oct was €514 €477

    Secure your holiday with a 30% deposit* Book now
  • A garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
    27
    Cove Castle, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    2-minute walk to Sandsfoot beach and the South West Coast path. (Ref. 994582)

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

    3 nights from Sun 25th Oct €808

    Secure your holiday with a 30% deposit*
    Last booked 1 hour ago
    Book now
  • Exterior view of a white townhouse with blue doors and railings and stone columns at Hops House in Brewers Quay Harbour
    25
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. (Ref. 994277)

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

    3 nights from Sun 25th Oct €888

    Secure your holiday with a 30% deposit* Book now
  • A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
    24
    Greenhill, Dorset
    • 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 €683

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a wooden gate and a sign reading Salisbury Terrace surrounded by a garden at Jasmine Cottage in Kilmington Devon
    17
    Kilmington, Devon, Devon
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A traditional, pet-friendly, semi-detached cottage nestled in Kilmington, Devon. (Ref. 1096104)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Tue 27th Oct €439

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Ground Floor modern accommodation. (Ref. 994034)

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

    3 nights from Sun 25th Oct €522

    Secure your holiday with a 30% deposit* Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    3 nights from Fri 23rd Oct €836

    Secure your holiday with a 30% deposit* Book now
  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    Property has offers
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 30% off - Sat 1st Nov 2025 to 28th Feb 2026

    3 nights from Tue 27th Oct €736

    Secure your holiday with a 30% deposit* Book now
  • A brick semi detached house with white framed windows and a wooden fence in front at 8 Biddlecombe Orchard in Bridport
    22
    Bridport, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    8 Biddlecombe Orchard is a contemporary property resting in the town of Bridport, Dorset. (Ref. 1152418)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    3 nights from Tue 27th Oct €568

    Secure your holiday with a 30% deposit* Book now
  • A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. (Ref. 1091449)

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

    3 nights from Sun 25th Oct €612

    Secure your holiday with a 30% deposit* Book now
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