Upwey Cottages

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Your search returned 232 cottages.

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  • Two adjacent houses with black front doors and small porches with awnings and shrubs outside at Anvil House in Brewers Quay Harbour
    25
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A pretty little modern house just a few minutes walk from the harbourside and local amenities. (Ref. 993929)

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

    7 nights from £566

    Secure your holiday with a 30% deposit* 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

    • Dream Cottages 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 £631

    Secure your holiday with a 30% deposit* Book now
  • A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    An immaculate second-floor apartment resting in the centre of Weymouth. (Ref. 1059264)

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

    7 nights from £636

    Secure your holiday with a 30% deposit* Book now
  • A living room with a brown leather sofa blue armchair glass coffee table and television at Tides Corner in Bowleaze
    36
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A modern ground floor annex in Weymouth, just moments from the beach. (Ref. 994726)

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

    7 nights from £731

    Secure your holiday with a 30% deposit* Book now
  • A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. (Ref. 1091449)

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

    7 nights from £521

    Secure your holiday with a 30% deposit* Book now
  • Front entrance of Bay View Hotel with brick buildings and ivy on walls in Weymouth
    49
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    One @ No36 is a delightful duplex apartment with the beach on your doorstep, with the convenience of off-road parking, in Weymouth, Dorset. (Ref. 1162201)

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

    7 nights from £714

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A stone and blue wooden building with external staircases and balconies under a clear sky at Santiago House in Weymouth
    Property has offers
    45
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This charming, four-bedroom holiday home rests in Weymouth, Dorset. (Ref. 1043677)

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

    • 10% off - Mon 22nd Dec 2025 to 5th Jan 2026

    7 nights from £1167

    Secure your holiday with a 30% deposit* Book now
  • A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
    85
    Weymouth, Dorset
    • Sleeps18
    • Bedrooms9
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. (Ref. 1123341)

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

    7 nights from £2570

    Secure your holiday with a 30% deposit* Book now
  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from £486

    Secure your holiday with a 30% deposit* Book now
  • Exterior of a white two-story house with a pitched roof and blue front door at The White Cottage in Weymouth
    Property has offers
    51
    Weymouth, Dorset
    • Sleeps9
    • Bedrooms4
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A stunning, detached home resting in Weymouth, Dorset. (Ref. 1022573)

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

    • 10% off - Thu 30th Oct to 22nd Dec 2025

    7 nights from £1017

    Secure your holiday with a 30% deposit* Book now
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