Osmington Cottages

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  • A residential building with a door and window at The Watch House in Weymouth
    New property
    28
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

    • Dream Cottages rating

    The Watch House is a simply beautiful terraced townhouse nestled into the bustling seaside town of Weymouth, Dorset, close to shops and beaches. (Ref. 1205646)

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

    7 nights from From £884

    Book now
  • An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
    38
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. (Ref. 1137640)

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

    7 nights from From £639

    Book now
  • A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. (Ref. 1162203)

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

    7 nights from From £736

    Book now
  • A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
    Property has offers
    59
    Osmington, Dorset
    • Sleeps12
    • Bedrooms5
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Luxurious 5 star contemporary property. (Ref. 993982)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Swimming pool
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • £4417 off - Mon 28th Dec 2026 to 4th Jan 2027

    7 nights from From £3510

    Book now
  • A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A superb first-floor apartment resting in Weymouth, Dorest. (Ref. 1059262)

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

    7 nights from From £620

    Book now
  • A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
    56
    Weymouth, Dorset
    • Sleeps12
    • Bedrooms6
    • Pet FriendlyNo

      5.0★

      Perfect

    • Dream Cottages rating

    The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. (Ref. 1059621)

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

    7 nights from From £1073

    Book now
  • A patio with a table and chairs set outside a house with open glass doors and a large plant at Park Mews Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. (Ref. 1054948)

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

    7 nights from From £558

    Book now
  • A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
    31
    Preston, Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    7 nights from From £625

    Last booked yesterday
    Book now
  • A living room with a sofa and dining area at Betty's Buoy Weymouth
    28
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Betty’s Buoy is a stylish first-floor apartment in Weymouth, Dorset, with open-plan living and easy access to the beach. (Ref. 1168986)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from From £448

    Book now
  • A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. (Ref. 1133998)

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

    7 nights from From £602

    Book now
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