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Chesil Cottage Holidays

440 properties found

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

123 On The Sea - The Eaves

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£445

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 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

£486

A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
Offer

Ocean Retreat

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£773

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

123 On The Sea - Victoria’s Place

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£522

A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
Offer

Goliath

Brewers Quay Harbour, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£525

An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth

Fountain Cottage

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£512

A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour

Embassy

Brewers Quay Harbour, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£485

A street view of brick buildings including Bay View Hotel and a pop-up pizza shop at The Loft @ No36 in Weymouth

The Loft @ No36

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£502

A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth

5 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£511

A street view of terraced houses with white doors and windows at Angel Cottage in Weymouth

Angel Cottage

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£317

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

A garden with a table and chairs on a deck at Little Gem in Weymouth

Little Gem

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£719

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

£468

A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour

Monarch

Brewers Quay Harbour, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£562

A small dining area with a round glass table set for two and wicker chairs by two windows with ocean views at 6 The Beaches in Weymouth

6 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£456

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

£529

A living room with sofas and cushions near glass doors with curtains and a rug at Admirals Retreat in Weymouth

Admiral's Retreat

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£511

This collection of Chesil Beach holiday cottages places you by one of Dorset's most iconic landmarks. Forming part of the Jurassic Coast, a UNESCO World Heritage Site, this 18-mile-long shingle barrier beach stretches from West Bay to Portland. Couples and families seeking the great outdoors will delight in this wild and unique natural landscape.

Why Chesil Beach?

The bustling Chesil Beach is lined with cafés, bars and plenty of family-friendly attractions. Head to the Fine Foundation Chesil Beach Centre to learn more about marine life through interactive displays, alongside booking boat trips and wildlife activities! From your Chesil Beach accommodation, you'll have the Fleet Lagoon nature reserve within easy reach to spot birdlife and rare species below the surface. Looking to plan a fishing trip? West Bexington is one of the most popular spots along Chesil Beach for catching mackerel! If beachcombing and swimming are top of your list, visit West Bay and Chesil Cove, two more sheltered and idyllic spots to spend a leisurely day. You are guaranteed unforgettable sunsets and views along the Jurassic Coast, and maybe even dolphins and whales in the distance!

Places to Visit near Chesil Beach

If you fancy exploring further afield, Chesil Beach holiday cottages make a wonderful base for Dorset! Plenty of activities await in the seaside town of Weymouth, from SEA Life to Weymouth's vibrant harbour, whereas West Bay is a much smaller harbour with spectacular cliffs to behold. You'll also find the nearby Bridport for plenty of cultural attractions in a delightful market town. History lovers can wander through a Roman Town House and Dorset Museum in Dorchester, as well as the former home of Victorian novelist, Thomas Hardy. Alternatively, visit the Isle of Portland for sweeping sea views from the villages of Castletown and Easton.

Types of Dorset Holidays

Whether it's a Chesil Beach lodge or luxury apartment, there are a variety of properties to suit all preferences. For seafarers and sandcastle makers, browse this selection of Dorset coastal cottages for easy access to the beach. Country cottages in Dorset are a wonderful alternative if you'd prefer to be nestled in the heathland, forests and rolling hills. Hoping to bring your furry friends along to the dog-friendly Chesil Beach? Explore a variety of dog-friendly cottages in Dorset, whilst these luxury cottages in Dorset are extra-special retreats. If your holiday date is looming, don't worry, there are a range of last minute cottages in Dorset to choose from!

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