Holiday Cottages for October Half term

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A white house with a peaked roof a black front door and paving in front at Lobster Lookout in Swanage
    Property has offers
    42
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fantastic three-bedroom house resting in Swanage, Dorset. (Ref. 1102492)

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

    3 nights from Fri 30th Oct $1133

    Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    24
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    3 nights from Wed 28th Oct $771

    Book now
  • A stone house with a red tiled roof and glass doors surrounded by a garden and lawn at The Cosy Cowshed in Dalwood
    25
    Dalwood, Devon
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A beautiful and contemporary ground-floor dwelling set in the village of Dalwood, East Devon. (Ref. 1060217)

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

    3 nights from Tue 27th Oct $662

    Book now
  • An outdoor area with a table and umbrella at Corner Barn in Winterborne Stickland
    Property has offers
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

    • 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 $535

    Book now
  • 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 Sun 25th Oct $801

    Book now
  • 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 $731

    Book now
  • A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. (Ref. 1078324)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Wed 28th Oct $670

    Book now
  • A gravel driveway in front of a building with large windows and a slate roof at The Courtyard - Hilltop Barn in Winterborne Zelston near Wareham
    41
    Winterborne Zelston near Wareham, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A beautiful detached barn conversion situated in the lovely Dorset area of Winterborne Zelston near Wareham and Wimborne Minster. (Ref. 1058078)

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

    3 nights from Fri 23rd Oct $878

    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 Fri 30th Oct $622

    Last booked yesterday
    Book now
  • A house with windows and a garden at June Cottage in Wool
    35
    Wool, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    June Cottage is a lovely cottage situated on the outskirts of Wool in Dorset, allowing pets and is well-situated to nearby attractions and amenities. (Ref. 1181945)

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

    3 nights from Sun 25th Oct $847

    Book now
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