Short Breaks in Weymouth

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Your search returned 292 cottages.

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  • The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
    58
    Weymouth, Dorset
    • Sleeps13
    • Bedrooms6
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

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

    7 nights from £2268

    Secure your holiday with a 30% deposit* Book now
  • A house with garage and driveway at The Chocolate Box in Weymouth
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

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

    7 nights from £749

    Secure your holiday with a 30% deposit* Book now
  • Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
    42
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)

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

    7 nights from £903

    Secure your holiday with a 30% deposit* Book now
  • A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
    24
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. (Ref. 1096825)

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

    7 nights from £525

    Secure your holiday with a 30% deposit* Book now
  • A coastal view with boats on water and a hill in the background at Portland Pebble in Wyke Regis
    43
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    An enticing, semi-detached house sitting in Wyke Regis, Dorset. (Ref. 1097679)

    • Wi-fi
    • Off-road parking

    7 nights from £776

    Secure your holiday with a 30% deposit* Book now
  • Front exterior of a brick house with white-framed windows and door and garden shrubs with black chairs and table outside at Splash in Weymouth
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. (Ref. 1154894)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from £673

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
    46
    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A fabulous three-bedroom holiday home in Wyke Regis, Dorset. (Ref. 1103441)

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

    7 nights from £710

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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  • A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
    27
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Sleeping 4 cosy cottage in Weymouth. (Ref. 994605)

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

    7 nights from £610

    Secure your holiday with a 30% deposit* Book now
  • Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
    Property has offers
    30
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

    • 12% off - Fri 13th Feb to 28th Feb 2026

    7 nights from £1006

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • Two armchairs with striped cushions by bay windows overlooking a beach at Three @ No36 in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. (Ref. 1162204)

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

    7 nights from £669

    Secure your holiday with a 30% deposit* Book now
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