Chesil Beach Holiday Cottages

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Your search returned 352 cottages.

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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 £602

    Secure your holiday with a 30% deposit* Book now
  • The front exterior of a brick house with several windows a wooden door and a white garage door at Mariners Rest in Weymouth
    15
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. (Ref. 994377)

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

    7 nights from £608

    Secure your holiday with a 30% deposit* Book now
  • A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
    11
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A well-presented, ground-floor apartment in Weymouth, Dorset. (Ref. 1126298)

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

    7 nights from £443

    Secure your holiday with a 30% deposit* Book now
  • A brick semi detached house with white framed windows and a wooden fence in front at 8 Biddlecombe Orchard in Bridport
    22
    Bridport, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    8 Biddlecombe Orchard is a contemporary property resting in the town of Bridport, Dorset. (Ref. 1152418)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from £589

    Secure your holiday with a 30% deposit* Book now
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    7 nights from £1422

    Secure your holiday with a 30% deposit* Book now
  • The Old Post Office - 1127439 - photo 1
    Property has offers
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

    • Dream Cottages rating

    The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. (Ref. 1127439)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 15% off - Tue 18th Nov to 30th Nov 2025

    • 10% off - Sat 20th Dec to 27th Dec 2025

    7 nights from £598

    Secure your holiday with a 30% deposit* Book now
  • 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 £508

    Secure your holiday with a 30% deposit* Book now
  • A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. (Ref. 1123724)

    • Wi-fi

    7 nights from £557

    Secure your holiday with a 30% deposit* Book now
  • An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
    33
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. (Ref. 932161)

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

    7 nights from £689

    Secure your holiday with a 30% deposit* Book now
  • A white semi detached house with blue doors and a blue fence under a clear sky at Ashwood Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern 3 Storey house. (Ref. 993939)

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

    7 nights from £765

    Secure your holiday with a 30% deposit* Book now
Most relevant
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