Osmington Cottages

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Your search returned 207 cottages.

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  • 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 €703

    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 €688

    Secure your holiday with a 30% deposit* Book now
  • A living room with a beige sectional sofa and colorful cushions a wicker coffee table a small round white table with baked goods a lamp a chair with a pillow a dining area with wooden chairs and a table at Winkle Cottage in Weymouth
    Property has offers
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. (Ref. 1140944)

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

    • 5% off - Fri 3rd Apr to 2nd May 2026

    7 nights from €780

    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
    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

    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
    46
    Preston, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.8★

      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

    7 nights from €1604

    Secure your holiday with a 30% deposit* Book now
  • A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    7 nights from €594

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
    23
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    7 nights from €662

    Secure your holiday with a 30% deposit*
    Last booked 4 hours ago
    Book now
  • A balcony with a small wooden table and chairs overlooking a waterway and buildings at Harbour Hideaway in Weymouth
    16
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A second-floor apartment resting in Weymouth. (Ref. 1007302)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from €584

    Secure your holiday with a 30% deposit* 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
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

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

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

    7 nights from €686

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A living room with a TV on a white stand and a black sofa with animal print cushions at Sunny Days in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern refurbished terraced cottage in Weymouth, sleeping 4, short walk to the beach and town, WiFi, Off road parking for 1 car. (Ref. 994696)

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

    7 nights from €616

    Secure your holiday with a 30% deposit* Book now
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