Chesil Beach Holiday Cottages

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Your search returned 352 cottages.

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  • A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
    21
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. (Ref. 1144645)

    • Wi-fi
    • Baby-friendly

    7 nights from £557

    Secure your holiday with a 30% deposit* Book now
  • A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth
    24
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.1★

      Good

    • Dream Cottages rating

    Sleeps six in Weymouth, patio garden. (Ref. 994586)

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

    7 nights from £659

    Secure your holiday with a 30% deposit* Book now
  • A three story house with a beige exterior stone and concrete walls at Osprey House Portland
    27
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Detached, large and modern house for large group of friends or big family. (Ref. 994499)

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

    7 nights from £714

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • An outdoor patio with a glass table set with wine glasses cheese and fruit overlooking the sea at Ocean Wave in Greenhill
    Property has offers
    19
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Beautiful apartment, that welcomes one well behaved dog, located on the esplanade, perfect for discovering the delights of Weymouth. (Ref. 994451)

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

    • £467 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from £750

    Secure your holiday with a 30% deposit* Book now
  • A row of stone cottages with thatched roofs and white framed windows along a sloped street at Bramble Cottage in Burton Bradstock
    29
    Burton Bradstock, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Character cottage in Burton Bradstock, sleeping 5 people. (Ref. 994024)

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

    7 nights from £719

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
    18
    Weymouth, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Traditional cute cottage, in the town centre side of Weymouth harbour. (Ref. 994240)

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

    7 nights from £494

    Secure your holiday with a 30% deposit* Book now
  • A living room with a fireplace and kitchen visible at Fisherman’s Cottage
    New property
    27
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    Fisherman’s Cottage, a pleasant house nestled in Weymouth, Dorset, with an open-plan design, an enclosed courtyard and proximity to the beach and amenities. (Ref. 1172825)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £492

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a thatched roof beside a road with trees and bushes in Burton Bradstock
    70
    Burton Bradstock, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Alice's Cottage is a characterful, thatched cottage situated in Burton Bradstock, Dorset. (Ref. 1144638)

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

    7 nights from £712

    Secure your holiday with a 30% deposit* Book now
  • A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    7 nights from £532

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a thatched roof and white windows beside a road at Little Berwick Cottage in Burton Bradstock
    23
    Burton Bradstock, Dorset
    • Sleeps8
    • Bedrooms5
    • PetsYes

      4.1★

      Good

    • Dream Cottages rating

    Full of Character thatched cottage just outside Burton Bradstock. (Ref. 994004)

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

    7 nights from £783

    Secure your holiday with a 30% deposit* Book now
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