Weymouth Holiday Cottages

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Your search returned 29 cottages.

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  • Everdene - 932160 - photo 1
    29
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Excellent

    • 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 £569

    Secure your holiday with a 30% deposit* Book now
  • Shepherd Oak - 932158 - photo 1
    26
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Very 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 £521

    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 £405

    Secure your holiday with a 30% deposit* Book now
  • Casterbridge - 932161 - photo 1
    28
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Excellent

    • 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 £593

    Secure your holiday with a 30% deposit* Book now
  • Budmouth - 932157 - photo 1
    31
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Excellent

    • 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 £494

    Secure your holiday with a 30% deposit* Book now
  • 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 £593

    Secure your holiday with a 30% deposit* Book now
  • Oak Cottage - 955591 - photo 1
    29
    Bere Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    A modern country cottage located near the village of Bere Regis, Dorset. (Ref. 955591)

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

    7 nights from £584

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

      4.8★

      Excellent

    • 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 £494

    Secure your holiday with a 30% deposit* 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 £1027

    Secure your holiday with a 30% deposit* Book now
  • Keepers Cottage - 905895 - photo 1
    27
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Excellent

    • Helpful Holidays rating

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

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

    7 nights from £405

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