Weymouth Holiday Cottages

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Your search returned 25 cottages.

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  • 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
  • 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 £630

    Secure your holiday with a 30% deposit* Book now
  • 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 £653

    Secure your holiday with a 30% deposit* 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 £653

    Secure your holiday with a 30% deposit* Book now
  • Budmouth - 932157 - photo 1
    31
    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 £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 £386

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • Mill House - 990015 - photo 1
    50
    Maiden Newton, Dorset
    • Sleeps12
    • Bedrooms6
    • PetsYes

      3.8★

      Good

    • Helpful Holidays rating

    Stunning Grade II listed house, located in the Maiden Newton area of Dorchester. (Ref. 990015)

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

    7 nights from £1134

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  • Shepherd's Hut - 5188 - photo 1
    11
    Milborne St Andrew, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0★

      Perfect

    • Helpful Holidays rating

    A superb, detached barn conversion resting on the outskirts of Winterborne Whitechurch. (Ref. 5188)

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

    7 nights from £653

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    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 £973

    Secure your holiday with a 30% deposit* Book now
  • Ammonite Cottage - 975331 - photo 1
    40
    Wareham, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.6★

      Outstanding

    • Helpful Holidays rating

    Charming period cottage in the Dorset market town of Wareham. (Ref. 975331)

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

    7 nights from £915

    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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