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Chesil Beach Holiday Cottages

372 properties found

A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth

The Nightingale

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£602

A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth

Smugglers Cottage

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£653

A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth

Harbour Retreat

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£504

A living room with a sofa, chair, coffee table and television at 123 On The Sea – Victoria’s Place in Weymouth
New

123 On The Sea - Victoria’s Place

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£453

A window with champagne and glasses overlooking the sea at 123 On The Sea – The Eaves in Weymouth
New

123 On The Sea - The Eaves

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£453

An entrance with double doors and window at Frome Gazey in Frampton
New

Frome Gazey Barn

Frampton, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£525

A hallway with door opening to the sea at 123 On The Sea - The Cubby in Weymouth
New

123 On The Sea - The Cubby

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£423

A living room with furniture including a sofa and a dresser at 4 The Beaches in Weymouth
New

4 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£601

A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth

Little Brook

Nottington near Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£552

A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock

Village View

Burton Bradstock, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£525

A garden with flowering plants and shrubs in front of a stone building with a tiled roof at Middle Farm Annex in Long Bredy

Middle Farm Annex

Long Bredy, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£524

A mobile home with a deck and steps at The Hideaway in Portesham

The Hideaway

Portesham, Dorset

4 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£442

A stone cottage with a path leading to the door and a grassy field with a tree and sea in the background at Washingpools in West Bexington

Washingpools

West Bexington, Dorset

2 Guests
1 Beds
Pet Friendly

for 7 nights

From

£445

A house with a deck and garden at Little Retreat in Upwey

Little Retreat

Upwey, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£485

A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey

Sixpenny Cottage

Upwey, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£485

A single story white building with a grey roof and glass entrance surrounded by a wooden fence at Cliff Barn in Burton Bradstock

Cliff Barn

Burton Bradstock, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£515

A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth

Blue Waters

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£760

A white cottage with a garden and wooden archway surrounded by a fence at Willowbrook Cottage in Litton Cheney

Willowbrook Cottage

Litton Cheney, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£637

A small stone patio with a round table and chairs next to a wooden bench outside a stone house at Tiddlers Cottage in Uploders near Bridport

Tiddlers Cottage

Uploders near Bridport, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£407

A stone thatched roof cottage with white framed windows and a porch along a quiet street at Cobblers Cottage in Langton Herring

Cobblers Cottage

Langton Herring, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£498

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 villages on the Isle of Portland like Easton 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.

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