Portland Cottages

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Your search returned 62 cottages.

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  • Two beige houses with black doors and windows on a paved street at Jurassic Coast House in Portland
    Property has offers
    42
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Modern and comfortable holiday house for up to 8 people in the Isle of Portland. (Ref. 994310)

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

    • 5% off - Sat 6th Sep to 20th Dec 2025

    7 nights from £939

    Secure your holiday with a 30% deposit* 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
    • PetsYes

      4.8★

      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 £532

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A living room with two blue sofas a wooden coffee table a rug a TV a bookshelf and a fireplace at Ammonite Cottage Fortuneswell Portland
    32
    Fortuneswell Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Traditional Portland Cottage. (Ref. 993922)

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

    7 nights from £515

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
    23
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    7 nights from £567

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • The front exterior of a red brick house with white framed windows and a white front door at 74 Reap Lane Southwell near Weston
    30
    Southwell near Weston, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. (Ref. 1158199)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £471

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A small bay with several boats on the water a sandy beach and people near the shore with bushes and flower pots in the foreground at Beach View House in Wyke Regis
    28
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. (Ref. 1091445)

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

    7 nights from £794

    Secure your holiday with a 30% deposit* Book now
  • A modern residential area with brick and stone buildings a driveway and a streetlamp at Sea Gem in Castletown Portland
    43
    Castletown, Portland, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher

    7 nights from £922

    Secure your holiday with a 30% deposit* Book now
  • A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
    24
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Sleeps six in Weymouth, patio garden. (Ref. 994586)

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

    7 nights from £642

    Secure your holiday with a 30% deposit* Book now
  • A garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
    27
    Cove Castle, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    2-minute walk to Sandsfoot beach and the South West Coast path. (Ref. 994582)

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

    7 nights from £689

    Secure your holiday with a 30% deposit* Book now
  • A beachfront with kayaks lined up near houses and water at Fairways in Wyke Regis
    22
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. (Ref. 1047698)

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

    7 nights from £524

    Secure your holiday with a 30% deposit* Book now
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