Chesil Cottage Holidays

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Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 429 cottages

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Map View
A garden with flowering plants and shrubs in front of a stone building with a tiled roof at Middle Farm Annex in Long Bredy
40
Long Bredy, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A detached barn conversion set within the village of Long Bredy. Woodburning fire. WiFi. Weymouth 12 miles; Yeovil 20 miles. (Ref. 998739)

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

7 nights from $776

Last booked 2 days ago
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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from $869

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A garden with a lawn and shrubs beside a white house with a glass porch at Skylark in Portesham
42
Portesham, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.4★

    Good

  • Sykes rating

This fantastic detached bungalow is located in Portesham, Dorset. Sea views. Open fire. Off-road parking. Weymouth 7.7 miles; Dorchester 7.7 miles. (Ref. 1076553)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Games room

7 nights from $1306

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Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

7 nights from $1367

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A single story white building with a grey roof and glass entrance surrounded by a wooden fence at Cliff Barn in Burton Bradstock
27
Burton Bradstock, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A brightly decorated property resting within the village of Burton Bradstock, Dorset. Couples retreat. Pet-friendly. Close to amenities and beach. Bridport 3.1 miles; Weymouth 15.7 miles; Dorchester 15.5 miles; Yeovil 22.4 miles. (Ref. 1118787)

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

7 nights from $630

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An outdoor patio area with a wooden table and six wooden chairs in front of a modern concrete structure with large sliding glass doors at Standby Generator Bunker Ringstead near Weymouth
67
Ringstead near Weymouth, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)

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

7 nights from $1456

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A stone house with a thatched roof and a wooden fence around the property at Dairy Cottage in Abbotsbury
67
Abbotsbury, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Dairy Cottage is a delightful, three-bedroom thatched cottage resting on a working farm on the outskirts of Abbotsbury, Dorset. Rural views. Pet-friendly. Stylish. Woodburning stove. Weymouth 12.3 miles. (Ref. 1123043)

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

7 nights from $864

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Stone buildings covered with greenery along a street with a white gate at Market House in Abbotsbury
43
Abbotsbury, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $788

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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
28
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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

7 nights from $1048

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A white cottage with a garden and wooden archway surrounded by a fence at Willowbrook Cottage in Litton Cheney
28
Litton Cheney, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

This beautifully-presented cottage rests in the village of Litton Cheney in Dorset. Near to village pub. Countryside views. Off-road parking. Dorchester 10.2 miles; Yeovil 21.1 miles. (Ref. 1021813)

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

7 nights from $913

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A single-story house with a tiled roof and a paved driveway near the ocean at Beach Haven in West Bexington
33
West Bexington, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Detached chalet bungalow in West Bexington, Dorset. Large garden with sea views. Close to beach. WiFi. Abbotsbury 4.8 miles; Bridport 6.8 miles. (Ref. 1017936)

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

7 nights from $1749

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Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
39
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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

7 nights from $941

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A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
27
Brewers Quay harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Sleeping 4 cosy cottage in Weymouth. Close to harbour and all amenities. Gated development. (Ref. 994605)

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

7 nights from $791

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Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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

7 nights from $1211

Last booked 2 days ago
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A backyard with a glass conservatory attached to a stone and tile roof building and wooden outdoor furniture on a patio at Fossil Barn in Weymouth
18
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Contemporary barn conversion, close to the Dorset coast. Secluded garden. Solid oak flooring. Five minute drive to Weymouth. (Ref. 994207)

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

7 nights from $872

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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
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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

7 nights from $668

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A row of multi-colored buildings along a waterfront with a boat named Top Cat III docked at Safe Harbour Brewers Quay harbour
33
Brewers Quay harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Cosy, comfortable and luxurious three storey house in Weymouth. Perfect for families. WiFi. Courtyard. One dog welcome. Pub and shop 5 min. Beach 10 min. Dorchester 8 miles. (Ref. 994606)

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

7 nights from $1268

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A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
25
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)

  • Wi-fi
  • Off-road parking

7 nights from $676

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Two armchairs with striped cushions by bay windows overlooking a beach at Three @ No36 in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Smart TV. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162204)

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

7 nights from $806

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A coastal view with boats on water and a hill in the background at Portland Pebble in Wyke Regis
43
Wyke Regis, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

An enticing, semi-detached house sitting in Wyke Regis, Dorset. Sea views. Near the beach and coast. Balcony. Weymouth 3.3 miles; Isle of Portland 3.8 miles; Dorchester 10.3 miles. (Ref. 1097679)

  • Wi-fi
  • Off-road parking

7 nights from $1001

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Map View

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! For more unmissable things to do at Chesil Beach, visit our Weymouth travel guide.

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 Holiday

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!