Holiday Cottages for October Half term

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • An exterior view of a building with a door and windows and flower pots at the entrance at Sandy Haven in Swanage
    37
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Sandy Haven is a delightful, ground-floor apartment resting in Swanage, Dorset. (Ref. 1140492)

    • Wi-fi
    • Ground floor bedroom

    3 nights from Fri 30th Oct From $726

    Book now
  • A white house with a peaked roof a black front door and paving in front at Lobster Lookout in Swanage
    42
    Swanage, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A fantastic three-bedroom house resting in Swanage, Dorset. (Ref. 1102492)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    3 nights from Fri 30th Oct From $1109

    Last booked 2 days ago
    Book now
  • Three modern two story houses with green window frames and stone wall facades with a paved driveway and some plants at Pebbles Reach in Fortuneswell
    42
    Fortuneswell, Dorset
    • Sleeps7
    • Bedrooms3
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. (Ref. 1091335)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    3 nights from Sat 24th Oct From $924

    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
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.3★

      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 Fri 30th Oct From $649

    Book now
  • An outdoor seating area with a table and two chairs outside a small stone building at The Studio in Shaftesbury
    24
    Shaftesbury, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    An eye-catching stone cottage resting on the outskirts of Shaftesbury, Dorset. (Ref. 1008394)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Baby-friendly

    3 nights from Sat 24th Oct From $484

    Book now
  • Exterior view of a two-story house with wooden paneling a balcony and metal railing at 6 Inveravon in Christchurch
    31
    Christchurch, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.4★

      Good

    • Dream Cottages rating

    6 Inveravon is a charming holiday home near the beach in the waterside town of Christchurch in Dorset with an open-plan living space and welcoming pets. (Ref. 1162271)

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

    3 nights from Thu 29th Oct From $983

    Last booked 2 days ago
    Book now
  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    3 nights from Fri 23rd Oct From $797

    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
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Sat 24th Oct From $658

    Book now
  • The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Ground Floor modern accommodation. (Ref. 994034)

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

    3 nights from Fri 30th Oct From $610

    Book now
  • A patio with a metal table and two chairs outside a building with white framed windows and a glass door at 1 Cowdea Farm in Bettiscombe near Beaminster and Bridport
    Property has offers
    27
    Bettiscombe near Beaminster and Bridport, Dorset
    • Sleeps3
    • Bedrooms2
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A ground floor, semi-detached stone barn conversion on edge of Bettiscombe in Dorset. (Ref. 1857)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Washing machine
    • Baby-friendly

    • 5% off - Sat 1st Aug to 31st Aug 2026

    3 nights from Sat 24th Oct From $613

    Book now
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