Chesil Beach Holiday Cottages

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Your search returned 350 cottages.

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  • 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

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

    7 nights from £517

    Secure your holiday with a 30% deposit* Book now
  • A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    7 nights from £531

    Secure your holiday with a 30% deposit* Book now
  • An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour
    28
    Brewers Quay Harbour, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Four bedrooms in Kellaway Court, Weymouth. (Ref. 994219)

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

    7 nights from £839

    Secure your holiday with a 30% deposit*
    Last booked 2 hours ago
    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 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 row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    7 nights from £592

    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 £779

    Secure your holiday with a 30% deposit* Book now
  • A stone cottage with two light blue doors and white framed windows with flowers outside at Dormouse Cottage in Burton Bradstock
    Property has offers
    34
    Burton Bradstock, Dorset
    • Sleeps3
    • Bedrooms2
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A traditional, thatched cottage nestled in Burton Bradstock, close to Dorset's Jurassic Coast. (Ref. 1135014)

    • Wi-fi
    • Washing machine

    • 5% off - Sat 1st Nov 2025 to 28th Feb 2026

    7 nights from £478

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    7 nights from £626

    Secure your holiday with a 30% deposit* Book now
  • A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
    23
    Wyke Regis, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Off road parking. (Ref. 994270)

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

    7 nights from £608

    Secure your holiday with a 30% deposit* Book now
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