Holiday Cottages for October Half term

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Your search returned 424 cottages.

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  • A garden with a shed and a bench overlooking a body of water at Harbour View Mudeford in Christchurch
    Property has offers
    26
    Christchurch, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Luxury coastal ground floor property, located on Fishermans Bank, Mudeford. (Ref. 1006623)

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

    • 20% off - Wed 23rd Dec 2026 to 5th Jan 2027

    3 nights from Sun 25th Oct €813

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  • A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. (Ref. 1156408)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 25th Oct €569

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  • A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
    11
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A well-presented, ground-floor apartment in Weymouth, Dorset. (Ref. 1126298)

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

    3 nights from Sun 25th Oct €531

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  • A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
    43
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)

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

    3 nights from Wed 28th Oct €923

    Last booked 2 days ago
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  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    3 nights from Wed 28th Oct €748

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  • A large two-story house with multiple sliding glass doors and windows and outdoor seating on a grassy yard at Shutts House Garden Apartment in Coombe Bissett
    32
    Coombe Bissett, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Absolutely stunning, luxurious ground floor accommodation at the eastern end of Wiltshire's beautiful Chalke Valley. (Ref. 1016405)

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

    3 nights from Fri 23rd Oct €1217

    Book now
  • A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
    41
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1092449)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    3 nights from Sat 24th Oct €568

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  • A row of houses with a white picket fence and small garden in front at Smugglers Cottage in Christchurch
    Property has offers
    32
    Christchurch, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty, one-bedroom cottage resting in Christchurch, Dorset. (Ref. 1098695)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 40% off - Fri 27th Feb to 25th Sep 2026

    3 nights from Wed 28th Oct €734

    Book now
  • A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
    40
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. (Ref. 1100406)

    • Wi-fi
    • Dishwasher

    3 nights from Sat 24th Oct €744

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  • A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
    42
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    3 nights from Wed 28th Oct €707

    Last booked yesterday
    Book now
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