Osmington Cottages

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Your search returned 203 cottages.

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  • 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
    • PetsNo

      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

    7 nights from £457

    Secure your holiday with a 30% deposit* Book now
  • Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth
    19
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A terrace property resting close to the beach and harbour in Weymouth. (Ref. 1038344)

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

    7 nights from £594

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  • A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
    50
    Weymouth, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

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

    7 nights from £1025

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  • A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz
    28
    Sutton Poyntz, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. (Ref. 994009)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £458

    Secure your holiday with a 30% deposit* Book now
  • A brick and white building facade with multiple windows on Trinity Road
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A Grade II listed, spacious maisonette apartment over the first and second floor in the Dorset town of Weymouth. (Ref. 1011525)

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

    7 nights from £812

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  • A wooden house with skylights and a small garden area surrounded by trees at Roman Lodge in Osmington
    31
    Osmington, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A bright and airy lodge resting in Osmington near Preston, Dorset. (Ref. 1093891)

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

    7 nights from £720

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  • A window view of a harbor with sailboats and buildings in the background at The Ferryman in Weymouth
    16
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A character-filled cottage located in the popular seaside town of Weymouth, Dorset. (Ref. 1017295)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £599

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  • A garden with grass and flowerbeds in front of a blue bungalow with a veranda and outdoor chairs at Harbour View Bungalow in Weymouth
    30
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Overlooking the beautiful Nothe Gardens and, through the trees, the coastal views of Weymouth Bay and Portland Harbour is Harbour View Bungalow. (Ref. 994244)

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

    7 nights from £1206

    Secure your holiday with a 30% deposit* Book now
  • A house with a pink door on a street at Shrimp Cottage in Brewers Quay Harbour
    Property has offers
    37
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. (Ref. 1173548)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 15% off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from £660

    Secure your holiday with a 30% deposit* Book now
  • A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    An immaculate second-floor apartment resting in the centre of Weymouth. (Ref. 1059264)

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

    7 nights from £648

    Secure your holiday with a 30% deposit* Book now
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