Holiday Cottages for October Half term

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Your search returned 454 cottages.

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  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Sun 26th Oct $544

    Secure your holiday with a 30% deposit* Book now
  • A waterfront with boats and buildings including Buccaneer Cottage at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • 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 1st Nov $946

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A thatched roof cottage with a path leading through a lawn and a garden at Thatch Cottage in Buckland Newton
    27
    Buckland Newton, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    A traditional, thatched cottage situated within the village of Buckland Newton, Dorset. (Ref. 1132784)

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

    3 nights from Fri 24th Oct $825

    Secure your holiday with a 30% deposit* Book now
  • Stone terraced houses with red doors and red leafy trees behind wooden fences
    18
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sea Breeze is a lovely, terraced cottage resting in the outskirts of Swanage, Dorset. (Ref. 1150773)

    • Wi-fi
    • Off-road parking

    3 nights from Mon 3rd Nov $570

    Secure your holiday with a 30% deposit* Book now
  • A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    3 nights from Sun 26th Oct $645

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A living room with two blue sofas a wooden coffee table a rug a TV a bookshelf and a fireplace at Ammonite Cottage Fortuneswell Portland
    32
    Fortuneswell Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Traditional Portland Cottage. (Ref. 993922)

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

    3 nights from Fri 24th Oct $682

    Secure your holiday with a 30% deposit* Book now
  • A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
    21
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. (Ref. 1144645)

    • Wi-fi
    • Baby-friendly

    3 nights from Sun 26th Oct $710

    Secure your holiday with a 30% deposit* Book now
  • A stone and brick cottage with a tiled roof and a small garden beside a road at Way's Forge in Piddlehinton
    24
    Piddlehinton, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. (Ref. 994768)

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

    3 nights from Sun 2nd Nov $626

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    3 nights from Sun 26th Oct $821

    Secure your holiday with a 30% deposit* Book now
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    3 nights from Sat 1st Nov $1490

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
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