Southwell Cottages

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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
  • A balcony with glass table and chairs overlooking buildings and a body of water at Panoramic View in Castletown Portland
    Property has offers
    22
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.2★

      Good

    • Dream Cottages rating

    A well-presented, modern apartment on the rugged Isle of Portland. (Ref. 1034885)

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

    • 5% off - Mon 22nd Jun to 4th Sep 2026

    7 nights from From £519

    Last booked yesterday
    Book now
  • Exterior view of a row of houses with bay windows a blue door and a plant in a pot at The Shambles in Fortuneswell
    25
    Fortuneswell, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.3★

      Good

    • Dream Cottages rating

    A well-presented two-bedroom cottage resting in Fortuneswell in Dorset. (Ref. 1082838)

    • Wi-fi
    • Dishwasher

    7 nights from From £620

    Last booked 3 hours ago
    Book now
  • A coastal town with houses along the shoreline and a beach at The View in Portland
    29
    Portland, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Bright contemporary property perfect groups of guests in the Isle of Portland. (Ref. 994754)

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

    7 nights from From £787

    Book now
  • A cream colored two story house with blue window frames and a blue front door at Fisherman's Cottage King Street in Fortuneswell
    36
    Fortuneswell, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.4★

      Good

    • Dream Cottages rating

    Fisherman's Cottage, King Street, is a charming cottage resting in Fortuneswell, Dorset. (Ref. 1152166)

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

    7 nights from From £472

    Book now
  • A backyard with a hot tub, a table with chairs, an umbrella, grass, trees, and a wooden fence at Cliffwalk Cottage in Southwell
    26
    Southwell, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.2★

      Good

    • Dream Cottages rating

    This contemporary holiday home rests in Portland, Dorset. (Ref. 1122555)

    • Pets go free
    • Wi-fi
    • Hot Tub
    • Dishwasher
    • Washing machine

    7 nights from From £441

    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
    • Pet FriendlyNo

      4.9★

      Outstanding

    • 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

    7 nights from From £644

    Book now
  • A row of attached houses with different exterior finishes on a street at Home From Home in Fortuneswell
    57
    Fortuneswell, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Home From Home is a delightful cottage nestled in the village of Fortuneswell in Dorset, Isle of Portland and is pet-friendly and near the beach. (Ref. 1158103)

    • Pets go free
    • Wi-fi
    • Washing machine

    7 nights from From £472

    Book now
  • A dining area with round wooden table and chairs next to sliding glass doors leading outside with sofas and kitchen stools in Mermaid Cottage in Wakeham Portland
    29
    Wakeham, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.0★

      Good

    • Dream Cottages rating

    Mermaid Cottage is a delightful, contemporary cottage close to a beach and amenities, in the village of Wakeham, on the Isle of Portland, in Dorset. (Ref. 1143548)

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

    7 nights from From £504

    Book now
  • A stone house with windows and a garden with bushes in front at Anchor Cottage in Weston Portland
    35
    Weston, Portland, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Anchor Cottage is a traditional 19th-century Portland Stone cottage resting in the charming village of Weston, Portland, Dorset, with off-road parking. (Ref. 1160217)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from From £504

    Last booked yesterday
    Book now
  • The exterior corner of a building with blue beams a glass door partially open and a sign that reads Groves House at Groves House Castletown near Fortuneswell
    17
    Castletown near Fortuneswell, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyNo

      4.2★

      Good

    • Dream Cottages rating

    Groves House is a lavish, reverse-level abode located in Castletown near Fortuneswell in Dorset, with an open-plan layout and only a short walk from a pub. (Ref. 1166808)

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

    7 nights from From £483

    Book now
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