Osmington Cottages

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Your search returned 203 cottages.

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  • Front view of two adjoining houses with black doors and white brick walls with a paved driveway at Maisy Cottage in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern and beautiful cottage in the heart of Weymouth. (Ref. 994369)

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

    7 nights from €645

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a stone and brick house with multiple windows and blue doors a patio with chairs a table and an umbrella and plants at The Gables in Brewers Quay Harbour
    18
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Lovely 4 bedroom house in gated area. (Ref. 994213)

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

    7 nights from €935

    Secure your holiday with a 30% deposit* Book now
  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    7 nights from €646

    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
    Property has offers
    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

    • 5% off - Sat 23rd Aug to 30th Aug 2025

    7 nights from €903

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • Stone cottage with thatched roof behind a metal gate and garden at Lychgate Cottage Osmington
    42
    Osmington, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Two bedroomed coastal village location. (Ref. 994364)

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

    7 nights from €714

    Secure your holiday with a 30% deposit* Book now
  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    7 nights from €763

    Secure your holiday with a 30% deposit* Book now
  • 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
    Property has offers
    18
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.4★

      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

    • 5% off - Sat 6th Sep to 30th Sep 2025

    7 nights from €967

    Secure your holiday with a 30% deposit* Book now
  • A stone house with a tiled roof and a paved driveway at Sunningdale Rise in Preston
    Property has offers
    46
    Preston, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

    • Dream Cottages rating

    Sunningdale Rise is a striking, detached home on a gated development with off-road parking, close to a beach, in the village of Preston in Dorset. (Ref. 1149947)

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

    • 10% off - Fri 13th Jun to 25th Jul 2025

    7 nights from €1617

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. (Ref. 994201)

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

    7 nights from €739

    Secure your holiday with a 30% deposit*
    Last booked 9 hours ago
    Book now
  • A window view of a harbor with sailboats and buildings in the background at The Ferryman in Weymouth
    16
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.7★

      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 €746

    Secure your holiday with a 30% deposit* Book now
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