Chesil Beach Holiday Cottages

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Your search returned 350 cottages.

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  • A window view of a harbor with sailboats and buildings in the background at The Ferryman in Weymouth
    16
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A character-filled cottage located in the popular seaside town of Weymouth, Dorset. (Ref. 1017295)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from €673

    Secure your holiday with a 30% deposit* Book now
  • A row of terraced houses with different colored facades along a street at Old Harbour Townhouse in Weymouth
    31
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. (Ref. 1159836)

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

    7 nights from €844

    Secure your holiday with a 30% deposit* Book now
  • Front view of a brick house with white framed windows a white door two black chairs and a palm tree at Reaver Brewers Quay harbour
    Property has offers
    27
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sleeping four near harbourside in Weymouth. (Ref. 994584)

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

    • €329 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from €793

    Secure your holiday with a 30% deposit* Book now
  • Front of a red brick terraced house with white door and windows and plants in front at Rockpools in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Sleeping four in Maltings area of Weymouth, pet friendly. (Ref. 994596)

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

    7 nights from €643

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with a white front door and a paved pathway bordered by trimmed hedges at Knapp Cottage in Chickerell
    39
    Chickerell, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A charming, three-bedroom cottage sitting in Chickerell, Dorset. (Ref. 1086432)

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

    7 nights from €734

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  • A dining area with a glass table set with plates wine glasses bread and flowers overlooking a living room with black sofas and large window at Harbourside Haven Penthouse 2 in Weymouth
    16
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A marvellous third-floor penthouse situated overlooking the harbour in Weymouth, Dorset. (Ref. 1059267)

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

    7 nights from €693

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. (Ref. 932160)

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

    7 nights from €793

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  • A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz
    28
    Sutton Poyntz, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. (Ref. 994009)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from €1134

    Secure your holiday with a 30% deposit* Book now
  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from €555

    Secure your holiday with a 30% deposit* Book now
  • A carport with gravel driveway and trees at The Halt in Maiden Newton
    Property has offers
    31
    Maiden Newton, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. (Ref. 1165359)

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

    • 20% off - Sat 20th Dec 2025 to 2nd Jan 2026

    • 10% off - Sat 3rd Jan to 31st Jan 2026

    7 nights from €377

    Secure your holiday with a 30% deposit* Book now
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