Chesil Beach Holiday Cottages

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Your search returned 334 cottages.

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    • Sleeps6
    • Bedrooms3
    • PetsYes
    • Dream Cottages rating

    Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. (Ref. 1153879)

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

    7 nights from £780

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

    The Lobster Pot, a nicely-presented apartment rests in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1151706)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from £528

    Secure your holiday with a 30% deposit*
    Last booked yesterday
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    • Sleeps18
    • Bedrooms9
    • PetsNo
    • Dream Cottages rating

    The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. (Ref. 1123341)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from £2540

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      3.9

      Good

    • Dream Cottages rating

    Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. (Ref. 1141828)

    • Wi-fi
    • Dishwasher

    7 nights from £552

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    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.6

      Outstanding

    • Dream Cottages rating

    Blue Yonder is a cheerful, terrace holiday home resting by the sea in Weymouth, Dorset. (Ref. 1144628)

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

    7 nights from £656

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    • Sleeps5
    • Bedrooms3
    • PetsNo
    • Dream Cottages rating

    Belvedere Cottage is a delightful holiday home nestled in the town of Weymouth, Dorset. (Ref. 1147966)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from £761

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    • Sleeps4
    • Bedrooms2
    • PetsYes
    • Dream Cottages rating

    26 High West is a beautifully-presented townhouse located near the harbour in the lovely town of Weymouth, Dorset. (Ref. 1135362)

    • Wi-fi
    • Dishwasher
    • Baby-friendly

    7 nights from £502

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    • 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 £704

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    Last booked yesterday
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    • Sleeps3
    • Bedrooms2
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Trinity is a pleasant holiday cottage resting in the coastal town of Weymouth, Dorset, Open-plan living space. (Ref. 1153512)

    • Wi-fi
    • Dishwasher
    • Baby-friendly

    7 nights from £527

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    Last booked 2 days ago
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    • Sleeps3
    • Bedrooms2
    • PetsNo
    • Dream Cottages rating

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

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

    7 nights from £669

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Our fantastic range of Chesil Beach holiday cottages will ensure your Dorset getaway will be one to remember. 

Why a Chesil Beach Holiday?

Chesil Beach is one of Dorset’s most iconic landmarks; an 18-mile long shingle beach stretching from West Bay to Portland. This wild and rugged beach is part of the Jurassic Coast World Heritage Site. Behind Chesil Beach lies the Fleet Lagoon; a large saline lake trapped between the pebble beach and the mainland. The lagoon is home to the Mute Swans of the Abbotsbury Swannery - the lagoon is the only place in the world where you can walk through a nesting colony. 

You can learn all about Chesil’s wildlife at the Chesil Beach Visitor Centre, where you can also enjoy a cuppa at the Taste Café or book a trip on the Fleet Explorer - a great way to explore the area. 

Places to Visit Near Chesil Beach

There are many places to explore during your Chesil Beach holiday, from the Isle of Portland and Southwell to West Bay and Bridport. The charming seaside town of Weymouth is one of the most popular towns along the South West Coast, with fun activities and attractions for all the family. Plus, the charming villages of Langton Herring and Osmington are just a short drive away. 

The iconic destinations of Corfe Castle, Durdle Door and Lulworth Cove are all just a short drive away too.

Types of Holiday 

From charming thatched cottages to harbourside apartments, we have an incredible range of holiday cottages available across Dorset. So whether you're looking to go on holiday with your dog or are looking for a cosy cottage with an open fire, then here at Dream Cottages we can make your holiday dreams a reality. Or why not whisk your other half away for Valentine's weekend for a romantic stay?

If you’re ready to book your Chesil Beach accommodation, then get in touch with one of our trusted travel experts today.