Holiday Cottages for October Half term

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Your search returned 125 cottages.

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  • Front view of two adjoining houses with black doors and white brick walls with a paved driveway at Maisy Cottage in Weymouth
    25
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern and beautiful cottage in the heart of Weymouth. (Ref. 994369)

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

    3 nights from Wed 29th Oct $747

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with white framed windows and a light green door along a street in a village
    20
    Burton Bradstock, Dorset
    • Sleeps4
    • Bedrooms3
    • PetsYes

      4.0★

      Good

    • Dream Cottages rating

    Thatched cottage in coastal village. (Ref. 994593)

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

    3 nights from Wed 29th Oct $937

    Secure your holiday with a 30% deposit* Book now
  • A house with outdoor seating area at Budmouth Upwey near Weymouth
    42
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. (Ref. 932157)

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

    3 nights from Wed 29th Oct $1007

    Secure your holiday with a 30% deposit* Book now
  • A living room with sofas and a television at Weyside in Weymouth
    New property
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Weyside is a fantastic apartment in the seaside town of Weymouth, located in Dorset, boasting close proximity to the beach as well as several amenities. (Ref. 1164944)

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

    3 nights from Wed 29th Oct $849

    Secure your holiday with a 30% deposit* Book now
  • A white two-story building with a blue door and black framed windows labeled Neptune Cottage in Fortuneswell
    20
    Fortuneswell, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      3.8★

      Good

    • Dream Cottages rating

    Neptune cottage situated in the Isle of Portland is very cosy and comfortable. (Ref. 994425)

    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Wed 29th Oct $782

    Secure your holiday with a 30% deposit* Book now
  • A small white house with a dark roof and black windows surrounded by potted plants and a gravel driveway with purple flowers in the foreground at Little England Cottage in Milborne St Andrew
    19
    Milborne St Andrew, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    A well-presented property resting on the outskirts of Milborne St Andrew. (Ref. 1017554)

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

    3 nights from Wed 29th Oct $603

    Secure your holiday with a 30% deposit* Book now
  • A building with apartments and boats at Harbourside Apartment Weymouth
    New property
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Harbourside Apartment is a waterfront retreat in Weymouth, Dorset, offering views of the town bridge and harbour with convenient access to amenities. (Ref. 1189387)

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

    3 nights from Wed 29th Oct $851

    Secure your holiday with a 30% deposit* Book now
  • An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze
    22
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    Sea Spray is a pleasant, open-plan holiday home perched on the edge of Bowleaze, Dorset, enjoying sea views and a short walk to a beach and a pub. (Ref. 1174075)

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

    3 nights from Thu 30th Oct $619

    Secure your holiday with a 30% deposit* Book now
  • A street view of a blue painted building with white framed windows and two white doors in a row of attached houses
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. (Ref. 1017563)

    • Ground floor bedroom
    • Dishwasher
    • Washing machine

    3 nights from Wed 29th Oct $1076

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with bay windows and a front door numbered 7 with adjacent houses at Seahorse Cottage in Weymouth
    21
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Delightful stone terraced cottage close to Old Harbour in Weymouth, Dorset. (Ref. 1000703)

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

    3 nights from Wed 29th Oct $784

    Secure your holiday with a 30% deposit* Book now
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