Upwey Cottages

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Your search returned 231 cottages.

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    • Sleeps9
    • Bedrooms4
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. (Ref. 1139723)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $1329

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8

      Outstanding

    • Dream Cottages rating

    Located in a quiet location in Weymouth, Upsidedown House is a unique and beautiful holiday home. (Ref. 994746)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • $385 off - Mon 29th Dec 2025 to 6th Jan 2026

    7 nights from $1188

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9

      Outstanding

    • Dream Cottages rating

    Link detached modern annex lodge in the Dorset Coastal village of Osmington. (Ref. 994794)

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

    7 nights from $678

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8

      Outstanding

    • Dream Cottages rating

    This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1037083)

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

    7 nights from $648

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    A delightful 3 storey fishermans cottage that has been beautifully restored in the harbour area of Weymouth. (Ref. 993928)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly

    7 nights from $811

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps6
    • Bedrooms3
    • PetsYes

      5.0

      Perfect

    • Dream Cottages rating

    Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. (Ref. 1173548)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $843

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    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    7 nights from $946

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    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    7 nights from $768

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3

      Good

    • Dream Cottages 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 $805

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    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    Cedar Drive is a charming house in Preston, Dorset, boasting ground-floor living, close proximity to local amenities and the coast for great days out. (Ref. 1173784)

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

    7 nights from $781

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Most relevant
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