Self-Catering Weymouth Cottages

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Your search returned 290 cottages.

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  • A stone cottage with a green door and white framed windows with a garden and flowers at Norden Cottage in Osmington
    33
    Osmington, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Norden Cottage is a fine, three-bedroom abode resting in Osmington, Dorset. (Ref. 1149647)

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

    7 nights from €833

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a brick terraced house with blue door white window and small hedge at Leo's Place in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A well-presented property nestled in the heart of Weymouth, Dorset. (Ref. 1134491)

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

    7 nights from €814

    Secure your holiday with a 30% deposit* Book now
  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    Property has offers
    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

    • €295 off - Sat 20th Dec to 27th Dec 2025

    • €278 off - Sat 27th Dec 2025 to 3rd Jan 2026

    7 nights from €825

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
    29
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    A well-presented, mid-terrace property resting within the village of Wyke Regis. (Ref. 1006910)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from €752

    Secure your holiday with a 30% deposit* Book now
  • Two beige houses with black doors and windows on a paved street at Jurassic Coast House in Portland
    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

    7 nights from €1154

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  • A window with binoculars on the sill looking out to buildings a clock tower and a marina at Anchorage View in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Anchorage View is a stunning, two-bedroom property resting in Weymouth, Dorset. (Ref. 1145912)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from €733

    Secure your holiday with a 30% deposit* Book now
  • A balcony with a round glass table and wicker chairs overlooking a marina and trees at Sunset View in Castletown Portland
    50
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    Sunset View is a perfectly-positioned, fifth-floor apartment residing in Castletown, Dorset. (Ref. 1141111)

    • Wi-fi
    • Dishwasher
    • Baby-friendly

    7 nights from €580

    Secure your holiday with a 30% deposit* Book now
  • A living room with sofas and a television at Weyside in Weymouth
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Weyside is a fantastic apartment in the seaside town of Weymouth, located in Dorset, boasting close proximity to the beach as well as several amenities. (Ref. 1164944)

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

    7 nights from €752

    Secure your holiday with a 30% deposit* Book now
  • A stone house with a tiled roof and a garage next to a paved driveway at St Johns View in Portland
    19
    Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    St. (Ref. 994677)

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

    7 nights from €718

    Secure your holiday with a 30% deposit* Book now
  • Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
    32
    Wakeham, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

    • Wi-fi
    • Washing machine

    7 nights from €584

    Secure your holiday with a 30% deposit* Book now
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