Osmington 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 row of brick houses with blue and turquoise front doors and white windows on a street at Chapelhay Cottage in Weymouth
    40
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      3.6★

      Good

    • Dream Cottages rating

    Chapelhay Cottage is a lovely, terraced cottage nestled into the seaside town of Weymouth, Dorset. (Ref. 1131030)

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

    7 nights from €721

    Book now
  • A corner with two purple chairs and a round glass table by windows with shutters overlooking the beach at High Tide in Weymouth
    31
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsNo

      3.7★

      Good

    • Dream Cottages rating

    Beautiful, Georgian seafront house, nestled in the lively town of Weymouth. (Ref. 1006583)

    • Wi-fi
    • Dishwasher
    • Baby-friendly

    7 nights from €1750

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  • A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
    23
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    All second floor. (Ref. 994293)

    • Wi-fi

    7 nights from €758

    Last booked yesterday
    Book now
  • A row of colorful waterfront houses with docks in front at The Boat House in Weymouth
    38
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.0★

      Good

    • Dream Cottages rating

    A superb, Grade II listed house set on the harbour side in Weymouth. (Ref. 1005020)

    • Wi-fi
    • Ground floor bedroom
    • Dishwasher
    • Washing machine

    7 nights from €1609

    Last booked yesterday
    Book now
  • A bedroom with a bed pillows a shelf with plants and books a mirror and wooden doors at Apple Tree Cottage in Upton near Ringstead Bay
    Property has offers
    20
    Upton near Ringstead Bay, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A charming single-storey cottage resting in Upton near Preston, Dorset. (Ref. 1129333)

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

    • 10% off - Fri 29th May to 26th Jun 2026

    7 nights from €529

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  • A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth
    18
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    Enjoyable holiday home close to the Old Harbour in Weymouth for large groups. (Ref. 994432)

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

    7 nights from €997

    Book now
  • A dining area with a long table set with plates glasses and bread surrounded by blue chairs and a kitchen with appliances and plants at Beachaven in Weymouth
    48
    Weymouth, Dorset
    • Sleeps15
    • Bedrooms7
    • PetsNo

      4.0★

      Good

    • Dream Cottages rating

    Beachaven is a charming holiday home, set over three floors, located in the popular resort of Weymouth in Dorset resting near the beach and amenities. (Ref. 1151664)

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

    7 nights from €1623

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  • A brick house with a red door and white framed windows behind a stone wall at Weybury Cottage in Brewers Quay Harbour
    18
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A period three-storey terraced property resting in Weymouth, Dorset. (Ref. 1055214)

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

    7 nights from €773

    Book now
  • A dining area with a wooden table, chairs, a bench, and table settings next to a living room with a sofa and a wall-mounted TV at Cove Street Cottage in Weymouth
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A well-positioned, three-storey home resting in Weymouth, Dorset. (Ref. 1122030)

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

    7 nights from €741

    Book now
  • The Old Post Office - 1127439 - photo 1
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. (Ref. 1127439)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from €595

    Book now
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