Osmington Cottages

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  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    7 nights from From $860

    Book now
  • A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in a gated complex near Weymouth harbour. (Ref. 994560)

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

    7 nights from From $950

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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
    25
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      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 From $777

    Book now
  • A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. (Ref. 1078324)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from From $752

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  • A living room with a TV on a stand a coffee table with board games a clock on the wall and large windows showing a sea view at Beach View Apartment 3 in Greenhill
    19
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Directly on the seafront. (Ref. 993989)

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

    7 nights from From $903

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  • 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
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from From $826

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  • A stone cottage with a thatched roof near the coast with grass and gravel paths at Pitt Cottage Ringstead
    30
    Ringstead, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Large kitchen diner. (Ref. 994553)

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

    7 nights from From $1236

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  • Front view of a brick house with white framed windows a white door two black chairs and a palm tree at Reaver Brewers Quay harbour
    27
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sleeping four near harbourside in Weymouth. (Ref. 994584)

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

    7 nights from From $932

    Book now
  • A driveway leading to a single-story brick house with a red door and a small front lawn at Sunny Haven in Preston
    26
    Preston, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A lovely two-bedroom bungalow resting in Preston, Dorset. (Ref. 1106680)

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

    7 nights from From $786

    Last booked 3 days ago
    Book now
  • A stone house with a tiled roof and a paved driveway at Sunningdale Rise in Preston
    Property has offers
    43
    Preston, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.7★

      Outstanding

    • 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 17th Jul to 2nd Oct 2026

    7 nights from From $1815

    Book now
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