Chesil Beach Holiday Cottages

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Your search returned 351 cottages.

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  • Exterior view of a stone house with multiple wooden windows and a wooden door next to outdoor dining furniture at The Granary Burton Bradstock
    33
    Burton Bradstock, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A beautifully presented property resting in the pretty village of Burton Bradstock. (Ref. 1069147)

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

    7 nights from $1372

    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 $931

    Secure your holiday with a 30% deposit* Book now
  • A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
    28
    Bowleaze, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A lodge sleeping four people, Bowleaze area of Weymouth. (Ref. 994500)

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

    7 nights from $1009

    Secure your holiday with a 30% deposit* Book now
  • A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A superb first-floor apartment resting in Weymouth, Dorest. (Ref. 1059262)

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

    7 nights from $816

    Secure your holiday with a 30% deposit* Book now
  • A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
    31
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. (Ref. 1162203)

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

    7 nights from $789

    Secure your holiday with a 30% deposit*
    Last booked 3 hours ago
    Book now
  • Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
    39
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This pretty, detached cottage lies in Preston, Dorset. (Ref. 1119018)

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

    7 nights from $872

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A semi detached house with a driveway and a garage at Lagoon View in Wyke
    33
    Wyke, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A charming cottage based in the village of Wyke Regis, Dorset. (Ref. 1121449)

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

    7 nights from $816

    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 $935

    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
    Property has offers
    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

    • $435 off - Mon 22nd Dec to 29th Dec 2025

    • $435 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from $824

    Secure your holiday with a 30% deposit* Book now
  • A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth
    18
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Beautiful seafront apartment within the popular resort of Weymouth in Dorset. (Ref. 1003083)

    • Wi-fi
    • Dishwasher

    7 nights from $644

    Secure your holiday with a 30% deposit* Book now
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