Weymouth Holiday Cottages

Your search returned 22 cottages.

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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
  • Exterior of a single story stone and brick cottage with black windows and doors and two flower pots at Keepers Cottage in Winterborne Stickland
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    Charming, characterful, single-storey barn conversion. (Ref. 905895)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from $633

    Last booked yesterday
    Book now
  • A stone house with a green front door four windows a grass lawn and a paved pathway at West Bay Holiday Home in West Bay
    Property has offers
    42
    West Bay, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    A superb, detached property nestled on a quiet residential estate in West Bay. (Ref. 1075057)

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

    • 10% off - Mon 25th May to 30th Jun 2026

    7 nights from $1296

    Book now
  • An outdoor area with a table and umbrella at Corner Barn in Winterborne Stickland
    Property has offers
    42
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • 10% off - Tue 5th May to 30th Jun 2026

    7 nights from $635

    Book now
  • A living room with two black leather sofas, a wood-burning stove, a wooden coffee table, a floor lamp, a small TV on a wooden stand, and glass doors with orange curtains at The Old Cart Shed in Winterborne Stickland
    Property has offers
    37
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    Exceptional, spacious rural barn conversion. (Ref. 905897)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • 10% off - Tue 5th May to 30th Jun 2026

    7 nights from $753

    Book now
  • A long brick and flint building with multiple doors and windows a grass lawn and flowers at The Old Stables in Winterborne Stickland
    Property has offers
    39
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • 10% off - Tue 5th May to 30th Jun 2026

    7 nights from $822

    Book now
  • An exterior view of a stone house with wooden windows and a gate by a roadside at The Old Barn in Harman's Cross near Swanage
    29
    Harman's Cross near Swanage, Dorset
    • Sleeps10
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Helpful Holidays rating

    Impressive barn conversion in rural Dorset location, close to beaches and Corfe Castle. (Ref. 906024)

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

    7 nights from $952

    Book now
  • Exterior view of a building with black doors and windows a wooden picnic table and umbrella on a patio at Rowdens Barn in Winterborne Stickland
    Property has offers
    36
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Beamed, single-storey holiday cottage near Winterborne Stickland. (Ref. 905898)

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

    • 5% off - Wed 1st Jul to 31st Aug 2026

    7 nights from $622

    Last booked yesterday
    Book now
  • An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
    33
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Helpful Holidays rating

    Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. (Ref. 932161)

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

    7 nights from $903

    Book now
  • A house with solar panels on the roof and a gravel driveway with plants in the foreground at The Old School Cottage in Tincleton near Dorchester
    61
    Tincleton, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Helpful Holidays rating

    Well-presented barn conversion, close to the rural Dorset hamlet of Tincleton. (Ref. 20691)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Dishwasher
    • Washing machine

    7 nights from $496

    Last booked 3 days ago
    Book now
  • A garden with furniture and a parasol at Maple Cottage Buckland Newton near Dorchester
    46
    Buckland Newton near Dorchester, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Helpful Holidays rating

    A tastefully decorated, semi-detached cottage resting near the Dorset town of Sturminster Newton. (Ref. 988550)

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

    7 nights from $633

    Book now
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