Weymouth Holiday Cottages

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Your search returned 23 cottages.

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  • The exterior wall of a yellow building with a white door and window and potted plants along the wall at Cuckoo Cottage in Bridport
    19
    Bridport, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    A romantic pied-a-terre in the bustling market town of Bridport. (Ref. 1004940)

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

    7 nights from £415

    Secure your holiday with a 30% deposit* Book now
  • A house with outdoor seating area at Budmouth Upwey near Weymouth
    42
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Helpful Holidays rating

    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. (Ref. 932157)

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

    7 nights from £616

    Secure your holiday with a 30% deposit* Book now
  • A brick house with a sunroom and patio furniture in a garden at South Lodge in Hazelbury Bryan
    30
    Hazelbury Bryan, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      5.0★

      Perfect

    • Helpful Holidays rating

    A beautifully furnished annexe cottage on the edge of the little hamlet of Hazelbury Bryan in Dorset. (Ref. 969185)

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

    7 nights from £394

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
    51
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Helpful Holidays rating

    Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. (Ref. 932158)

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

    7 nights from £616

    Secure your holiday with a 30% deposit* 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

      4.7★

      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 £695

    Secure your holiday with a 30% deposit* Book now
  • A stone pathway leads to a white house with a slate roof surrounded by trees and garden at Marles Farmhouse in Salwayash
    43
    Salwayash, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Beautiful converted farmhouse. (Ref. 976544)

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

    7 nights from £1415

    Secure your holiday with a 30% deposit* 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
    41
    West Bay, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7★

      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

    7 nights from £1011

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Helpful Holidays rating

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. (Ref. 932160)

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

    7 nights from £689

    Secure your holiday with a 30% deposit* 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
    27
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      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

    7 nights from £470

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    29
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Helpful Holidays rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

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

    7 nights from £747

    Secure your holiday with a 30% deposit* Book now
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Why book a cottage in Weymouth?

Weymouth is a bustling seaside town with a lovely,sandy beach nestled in a sheltered bay. The gentle, shallow waters make it a great destination for families with young children and there are also many family-friendly attractions close by, such as the sealife centre and sandworld sculpture park. Weymouth Harbour is often packed full of boats and just off the tip of the coast, reached by a causeway, is the Isle of Portland. It's great for outdoor adventurers as you can try rock climbing, abseiling and sailing. It is also a paradise for wildlife, with many rare birds choosing to stop here on their migratory path.

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