Weymouth Holiday Cottages

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Your search returned 27 cottages.

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  • Casterbridge - 932161 - photo 1
    28
    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 £692

    Secure your holiday with a 30% deposit* Book now
  • Shepherd Oak - 932158 - photo 1
    26
    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 £613

    Secure your holiday with a 30% deposit* Book now
  • The Old School Cottage - 20691 - photo 1
    54
    Tincleton near Dorchester, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.1★

      Good

    • Helpful Holidays rating

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

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

    7 nights from £382

    Secure your holiday with a 30% deposit* Book now
  • Bramshurst - 932159 - photo 1
    27
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. (Ref. 932159)

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

    7 nights from £613

    Secure your holiday with a 30% deposit* Book now
  • Cuckoo Cottage - 1004940 - photo 1
    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 £417

    Secure your holiday with a 30% deposit* Book now
  • The Old Stables - 18978 - photo 1
    24
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

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

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

    7 nights from £598

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • Little Orchard - 1037321 - photo 1
    39
    Maiden Newton, Dorset, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.2★

      Good

    • Helpful Holidays rating

    Lovely spacious family cottage in Maiden Newton Dorset.Enclosed large garden. (Ref. 1037321)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £889

    Secure your holiday with a 30% deposit* Book now
  • West Bay Holiday Home - 1075057 - photo 1
    38
    West Bay, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      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 £960

    Secure your holiday with a 30% deposit* Book now
  • The Mouse House - 986342 - photo 1
    12
    Milton Abbas, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.3★

      Good

    • Helpful Holidays rating

    Cosy, studio hideaway close to Milborne St Andrew in Dorset. (Ref. 986342)

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

    7 nights from £311

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • Everdene - 932160 - photo 1
    29
    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 £692

    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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