Holiday Cottages for October Half term

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Your search returned 146 cottages.

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  • A patio with wooden chairs and a table outside a brick building with open double doors at Hide-A-Way in Weymouth
    31
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

    • Dream Cottages rating

    Hideaway is a fine, single-storey annex situated in Weymouth, Dorset, with open-plan living, Smart TV, and well-positioned to nearby beaches and amenities. (Ref. 1169910)

    • Wi-fi
    • Ground floor bedroom
    • Baby-friendly

    3 nights from Mon 27th Oct $455

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A building with windows and a door at Lily's Pad in Weston, Portland
    25
    Weston, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    Lily's Pad is an intimate apartment in Weston, Dorset, with ground-floor living and is close to the picturesque coastline, alongside several amenities. (Ref. 1173596)

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

    3 nights from Mon 27th Oct $485

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a stone cottage with two white doors and two windows on a paved street at Jasmine Cottage in Swanage
    30
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.0★

      Good

    • Dream Cottages rating

    Jasmine Cottage is a well-positioned, characterful cottage resting in the heart of Swanage, Dorset. (Ref. 1132327)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 27th Oct $484

    Secure your holiday with a 30% deposit* Book now
  • A coastal town with rooftops and flowers in the foreground at 33 High Street in Fortuneswell
    39
    Fortuneswell, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    33 High Street is a well-positioned, three-bedroom home resting in Fortuneswell, Dorset. (Ref. 1138399)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 27th Oct $1076

    Secure your holiday with a 30% deposit* Book now
  • A small stone and wood house with a black door and climbing plants near stone steps and gravel ground at The Mouse House in Milton Abbas
    12
    Milton Abbas, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    Cosy, studio hideaway close to Milborne St Andrew in Dorset. (Ref. 986342)

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

    3 nights from Mon 27th Oct $469

    Secure your holiday with a 30% deposit* Book now
  • A row of terraced houses with different colored doors and upper windows at Braiders Rest in Bridport
    38
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Braiders Rest is a charming cottage located in the centre of Bridport, a market town in Dorset, with a lovely open-plan layout and short walk to a pub. (Ref. 1136101)

    • Wi-fi

    3 nights from Thu 30th Oct $594

    Secure your holiday with a 30% deposit* Book now
  • An outdoor view of a cottage with a thatched roof and stone wall at Bracken Cottage in
    New property
    10
    Osmington, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

    • Dream Cottages rating

    Bracken Cottage is a romantic property resting in the village of Osmington, Dorset, boasting an open-plan living area, is close to the beach and amenities. (Ref. 1173628)

    • Wi-fi
    • Off-road parking

    3 nights from Mon 27th Oct $1541

    Secure your holiday with a 30% deposit* Book now
  • A balcony with two chairs and a table overlooking a rocky shoreline and the sea at Sunset Lodge in Fortuneswell
    27
    Fortuneswell, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Sunset Lodge is a lovely retreat on Portland, moments from Chesil beach in Fortuneswell, Dorset, enjoying wonderful coastal views from the a balcony. (Ref. 1173296)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Mon 27th Oct $829

    Secure your holiday with a 30% deposit* Book now
  • A two story house with brick lower walls and pebble dash upper walls with multiple windows and a hedge in front at Deer Leap Cottage in Moreton
    24
    Moreton, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A fantastic semi-detached house resting on the outskirts or Moreton, Dorset. (Ref. 1060768)

    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Washing machine
    • Baby-friendly

    3 nights from Mon 27th Oct $987

    Secure your holiday with a 30% deposit* Book now
  • Stone cottages with colorful doors and decorative pavement in front at Poppy Cottage in Swanage
    18
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      3.6★

      Good

    • Dream Cottages rating

    A delightful mid-terrace cottage resting in Swanage, Dorset. (Ref. 1072835)

    • Wi-fi
    • Dishwasher

    3 nights from Mon 27th Oct $733

    Secure your holiday with a 30% deposit* Book now
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