Chesil Beach Holiday Cottages

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Your search returned 352 cottages.

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  • A pathway leading to a white house with a brown door surrounded by bushes and flowers at Lilliput in Shipton Gorge
    55
    Shipton Gorge, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Beautiful and cosy cottage located in a peaceful village of Shipton Gorge. (Ref. 994340)

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

    7 nights from $846

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a blue door and blue metal fence in front at Melanies Cottage Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. (Ref. 1146011)

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

    7 nights from $917

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with white doors and windows along a narrow road with plants and flowers growing at the base of the wall at Pippins Loders in Bridport
    29
    Bridport, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Stone three bedroom cottage near Bridport. (Ref. 994548)

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

    7 nights from $989

    Secure your holiday with a 30% deposit* Book now
  • A backyard patio with a glass table and chairs purple flowers a wooden bench and a wooden swing at Anchors Away in Weymouth
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A wonderful three-storey holiday cottage settled in the seaside resort of Weymouth in Dorset. (Ref. 1096129)

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

    7 nights from $899

    Secure your holiday with a 30% deposit* Book now
  • A pink house with open double doors and a picnic table on a grass lawn with a stone wall and countryside beyond at Cliff Farm No 2 Cottage Burton Bradstock
    23
    Burton Bradstock, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    A traditional farmhouse on the cliff top in Burton Bradstock, close to Hive Beach and it’s renowned café, West Bay, Wifi. (Ref. 994095)

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

    7 nights from $589

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  • A backyard with a brick house a blue wooden shed a small fenced garden and plants at Sandpiper in Weymouth
    41
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    A lovely one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1092449)

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

    7 nights from $636

    Secure your holiday with a 30% deposit* Book now
  • A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    7 nights from $1021

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  • A brick house with a brown door and windows a driveway wooden benches and a garage at Chickerell House Weymouth
    32
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. (Ref. 1152691)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom

    7 nights from $947

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
    Property has offers
    22
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. (Ref. 994201)

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

    • $463 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from $868

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of three adjacent terraced houses with bay windows and chimneys at Harbourside House in Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. (Ref. 994256)

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

    7 nights from $1587

    Secure your holiday with a 30% deposit* Book now
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