South West Dorset Accommodation

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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 house with large glass windows and a stone path leading to it surrounded by a garden at The Cart Barn in Ridge near Chilmark
    28
    Ridge near Chilmark, Wiltshire
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Fabulous conversion of a former cart shed set in peaceful surroundings and rolling countryside. (Ref. 988879)

    • Pet friendly (extra charges may apply)
    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from From €758

    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
    Property has offers
    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

    • 16% off - Sat 29th Aug to 5th Sep 2026

    7 nights from From €641

    Last booked yesterday
    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
    • Pet FriendlyNo

      4.8★

      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 From €690

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  • A garden with a table and chairs on a deck at Little Gem in Weymouth
    New property
    39
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

    • Dream Cottages rating

    Little Gem, a romantic ground-floor apartment resting in Weymouth, Dorset, boasts stunning coastal views and proximity to the beach and local amenities. (Ref. 1203646)

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

    7 nights from From €858

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  • The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
    26
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from From €619

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  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    7 nights from From €857

    Book now
  • A house with a fence and trees beside the road at Greenwich Cottage in Burton Bradstock
    New property
    36
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

    • Dream Cottages rating

    Greenwich Cottage is a welcoming, pet-friendly house near the beach in Burton Bradstock, Dorset, boasting off-road parking and ground-floor living. (Ref. 1206672)

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

    7 nights from From €865

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  • A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth
    36
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. (Ref. 1164179)

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

    7 nights from From €594

    Book now
  • A living room with leather sofas glass coffee table and large windows overlooking a marina at Harbourside Haven Penthouse 1 in Weymouth
    16
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.4★

      Good

    • Dream Cottages rating

    An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. (Ref. 1059266)

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

    7 nights from From €701

    Book now
  • Exterior view of a brick building with balconies windows and surrounding garden at Ocean Watch 5 in Greenhill
    17
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      4.4★

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    7 nights from From €804

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