Portland 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 garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
    27
    Cove Castle, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      4.8★

      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 From £712

    Book now
  • A balcony with two chairs a table with a bottle of champagne and glasses overlooking greenery and water at Waters Edge in Wyke Regis
    35
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern family house located on the edge of Weymouth, with sea views. (Ref. 994759)

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

    7 nights from From £674

    Last booked 2 days ago
    Book now
  • A semi detached house with a driveway and a garage at Lagoon View in Wyke
    33
    Wyke, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A charming cottage based in the village of Wyke Regis, Dorset. (Ref. 1121449)

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

    7 nights from From £648

    Book now
  • A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
    27
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)

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

    7 nights from From £561

    Book now
  • A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
    46
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fabulous three-bedroom holiday home in Wyke Regis, Dorset. (Ref. 1103441)

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

    7 nights from From £711

    Book now
  • A row of brick terraced houses with white doors and windows along a street at Castle Cove View in Castle Cove
    Property has offers
    26
    Castle Cove, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Wonderfully positioned townhouse just moments from Sandsfoot beach and the South West Coast path. (Ref. 1059103)

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

    • 5% off - Fri 7th Aug to 14th Aug 2026

    7 nights from From £801

    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

    7 nights from From £713

    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
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    7 nights from From £608

    Book now
  • A garden with a table and chairs on a deck at Little Gem in Weymouth
    New property
    39
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

    • Dream Cottages rating

    Little Gem, a romantic ground-floor apartment resting in Weymouth, Dorset, boasts stunning coastal views and proximity to the beach and local amenities. (Ref. 1203646)

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

    7 nights from From £734

    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
    • Pet FriendlyYes

      4.4★

      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)

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

    7 nights from From £465

    Book now
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