Holiday Cottages for October Half term

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Your search returned 431 cottages.

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  • Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington
    21
    Osmington, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    A charming thatched roof character cottage resting in the village of Osmington, Dorset. (Ref. 1064960)

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

    3 nights from Sat 24th Oct £494

    Book now
  • A two-story house surrounded by trees and shrubs with a grass lawn in front at The Old Post Office Cottage in Wareham
    46
    Wareham, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    A delightful detached house, set in large gardens, that will evoke feelings of being in an Enid Blyton Story. (Ref. 994562)

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

    3 nights from Fri 23rd Oct £965

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  • An outdoor patio with a wooden table and chairs an umbrella fruit basket and ocean view at Seacliff in West Bay
    32
    West Bay, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    High quality accommodation located in one of Dorset’s popular areas of West Bay. (Ref. 994629)

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

    3 nights from Fri 23rd Oct £906

    Book now
  • A stone building with white framed windows and a door along a paved street in a residential area at Brewers Retreat in Weymouth
    Property has offers
    22
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. (Ref. 1114655)

    • Wi-fi
    • Washing machine

    • 10% off - Wed 4th Mar to 30th Apr 2026

    3 nights from Sat 24th Oct £556

    Last booked yesterday
    Book now
  • Exterior view of a brick terraced house with blue door white window and small hedge at Leo's Place in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A well-presented property nestled in the heart of Weymouth, Dorset. (Ref. 1134491)

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

    3 nights from Sun 25th Oct £563

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  • A cottage with a thatched roof and a garden at Happiness Cottage in Piddlehinton
    Property has offers
    35
    Piddlehinton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    Happiness Cottage is a character cottage with a contemporary style, woodburning stove and enclosed garden resting in the village of Piddlehinton in Dorset. (Ref. 1175141)

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

    • 15% off - Wed 18th Feb to 30th Apr 2026

    3 nights from Sun 25th Oct £483

    Book now
  • A narrow street with houses and a view of the water at Blanche Cottage Brewers Quay Harbour
    45
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A fabulous, three-storey home resting near Weymouth's Old Harbour in Dorset. (Ref. 1092575)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 23rd Oct £695

    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 £608

    Book now
  • The exterior of a white terraced house with blue doors and window sills at South Harbour Cottage in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    A pretty, renovated terraced cottage, close to the old harbour and Brewers Quay in Weymouth. (Ref. 1043009)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 23rd Oct £592

    Book now
  • A row of terraced houses on a street with paved sidewalk and cobblestone road at Lobster Cottage Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Lovely and comfortable cottage next to the harbour in Weymouth. (Ref. 994351)

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

    3 nights from Sun 25th Oct £497

    Last booked 2 days ago
    Book now
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