Osmington Cottages

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Your search returned 203 cottages.

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  • A living room with leather sofas glass coffee table and large windows overlooking a marina at Harbourside Haven Penthouse 1 in Weymouth
    16
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. (Ref. 1059266)

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

    7 nights from $820

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a blue door and blue metal fence in front at Melanies Cottage Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. (Ref. 1146011)

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

    7 nights from $964

    Secure your holiday with a 30% deposit* Book now
  • Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. (Ref. 1058438)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $815

    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

      4.1★

      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 $865

    Secure your holiday with a 30% deposit* Book now
  • A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. (Ref. 993976)

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

    7 nights from $1612

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • Exterior view of a brick building with balconies windows and surrounding garden at Ocean Watch 5 in Greenhill
    17
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    7 nights from $904

    Secure your holiday with a 30% deposit* Book now
  • A front view of a three-story end terrace house with a lawn and driveway at The Ferns in Weymouth
    25
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Comfortable family seaside holiday home in Weymouth. (Ref. 994187)

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

    7 nights from $1087

    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

    • $325 off - Sat 27th Dec 2025 to 3rd Jan 2026

    7 nights from $964

    Secure your holiday with a 30% deposit* Book now
  • A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    7 nights from $1028

    Secure your holiday with a 30% deposit* Book now
  • A street view showing old and new boathouse buildings and inner harbour with boats in the background at Old Boathouse Weymouth
    23
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Centrally located in Weymouth beautiful holiday home for family or friends. (Ref. 994461)

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

    7 nights from $847

    Secure your holiday with a 30% deposit* Book now
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