Chesil Cottage Holidays

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Chesil Cottage Holidays

REFINE SEARCH

Your Chesil Beach, Dorset search returned 429 cottages

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Map View
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

    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 £706

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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

    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 £500

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A street view of terraced houses with white doors and windows at Angel Cottage in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

A characterful one-bedroom property resting in Weymouth, Dorset. Close to amenities and a beach. Near an AONB. Couples retreat. Dorchester 6.8 miles; Bridport 18.3 miles. (Ref. 1125691)

  • Wi-fi

7 nights from £317

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A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
14
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £714

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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
45
Uploders near Bridport, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. Enclosed garden. Romantic. In an AONB. Close to amenities. West Bay 5 miles; Lyme Regis 14.1 miles. (Ref. 1117867)

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

7 nights from £403

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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
18
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

Beautiful seafront apartment within the popular resort of Weymouth in Dorset. Incredible sea views. WiFi. Centre of Weymouth. (Ref. 1003083)

  • Wi-fi
  • Dishwasher

7 nights from £498

Last booked 3 days ago
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A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
18
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £473

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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
16
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

A cosy stone cottage for two this is the ideal place to spend quality time together, walking and exploring the local area. (Ref. 994208)

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

7 nights from £499

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A wooden exterior garage with gravel driveway and plants in pots at The Halt in Maiden Newton
Offer
22
Maiden Newton, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. West Bay 12.2 miles; Weymouth 17.2 miles; Lyme Regis 22.7 miles (Ref. 1165359)

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

  • 20% off - Fri 2nd May to 30th Jun 2025

  • 20% off - Tue 1st Jul to 31st Aug 2025

  • 10% off - Mon 1st Sep to 30th Sep 2025

7 nights from £392

Last booked 2 days ago
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A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £476

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A stone cottage with two windows a door and potted plants on a gravel yard with stone steps and greenery at Mill Cottage in Upwey
30
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

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

7 nights from £919

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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

    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 £1010

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A stone house with a tiled roof and a garage next to a paved driveway at St Johns View in Portland
Offer
19
Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

St. John’s View is a modern holiday home in the Isle of Portland with sea views. Over lower ground floor and ground floor. Shop, pub, beach 5 min. Weymouth 4.6 miles. (Ref. 994677)

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

  • 5% off - Sun 1st Jun to 30th Jun 2025

7 nights from £629

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A marina with boats docked and buildings in the background at Harbourside Haven Apartment 2 in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)

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

7 nights from £649

Last booked yesterday
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The exterior of a house with white walls and wooden paneling a patio area with a table umbrella and chairs at Whitegates Lodge in Osmington
15
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

Link detached modern annex lodge in the Dorset Coastal village of Osmington. Wifi. Parking for two cars. Short drive to Weymouth. (Ref. 994794)

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

7 nights from £578

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A brick house with white framed windows and door with two black chairs and a small table outside at Nuke in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Sykes Rating

This cottage boast style, character, and a fabulously contemporary interior. Central location. Surrounded by history. WiFi. Rodwell 0.9 miles. (Ref. 1005313)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £637

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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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

7 nights from £600

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A stone barn with wooden doors and windows with a paved patio and picnic bench with grass and gates at Warehams Barn in Puncknowle near Burton Bradstock
36
Puncknowle near Burton Bradstock, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

A superb barn conversion resting in Puncknowle near Burton Bradstock, Dorset. WiFi. Balcony. Rural location. Bridport 6.5 miles; Weymouth 12.9 miles; Swanage 38.7 miles. (Ref. 1098014)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £629

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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)

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

7 nights from £666

Last booked yesterday
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A living room with leather sofas glass coffee table and a television near large windows overlooking boats at Harbourside Haven Apartment 4 in Weymouth
Offer
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A stylish and contemporary apartment overlooking Weymouth Harbour in Dorset. Balcony. Underfloor heating. Smart TV. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059265)

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

  • 10% off - Sat 7th Jun to 2nd Aug 2025

7 nights from £666

Last booked 2 days ago
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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!