Chesil Beach Holiday Cottages

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Your search returned 352 cottages.

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  • A living room with two sofas a small white table with wine glasses and bottle a tv and glass doors to a garden at Pebbles in Burton Bradstock
    20
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Stylishly renovated bungalow in Burton Bradstock. (Ref. 994537)

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

    7 nights from $939

    Secure your holiday with a 30% deposit* Book now
  • The front entrance of a building with a dark door numbered 38 and a curved window with plants along the path at Flat 2 38 Preston Road Weymouth
    29
    Weymouth, Dorset
    • 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

    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 $816

    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 $685

    Secure your holiday with a 30% deposit* 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 $1534

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a house with white walls and wooden paneling a patio area with a table umbrella and chairs at Whitegates Lodge in Osmington
    15
    Osmington, Dorset
    • 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

    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 $939

    Secure your holiday with a 30% deposit*
    Last booked 6 hours ago
    Book now
  • A row of brick terraced houses with bay windows and small front gardens at Covecastle Cottage in Weymouth
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. (Ref. 994072)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $678

    Secure your holiday with a 30% deposit* Book now
  • An outdoor patio with a table and chairs overlooking a garden and sea at Blue Yonder in Weymouth
    37
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Blue Yonder is a cheerful, terrace holiday home resting by the sea in Weymouth, Dorset. (Ref. 1144628)

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

    7 nights from $792

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
    51
    Upwey near Weymouth, Dorset
    • 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

    Secure your holiday with a 30% deposit* Book now
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