Chesil Cottage Holidays

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Chesil Cottage Holidays

Your Chesil Beach, Dorset search returned 440 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A stone thatched roof cottage with white framed windows and a porch along a quiet street at Cobblers Cottage in Langton Herring
1 of 44
5
Langton Herring, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. Abbotsbury 5 miles; Weymouth 5.5 miles; Portland 9.4 miles; Dorchester 9.9 miles. (Ref. 1171904)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €561

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Stone buildings covered with greenery along a street with a white gate at Market House in Abbotsbury
1 of 43
5
Abbotsbury, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • 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


for 7 nights From €682

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A living room with a sofa and dining table at Red Rose Apartment in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms1
  • Pet FriendlyNo

  • Sykes rating

Red Rose Apartment is a centrally located apartment resting in Weymouth, Dorset and boasts parking, sea views and is within walking distance of the beach. Dorchester 7.8 miles; Bridport 19 miles. (Ref. 1190887)

  • Wi-fi
  • Washing machine


for 7 nights From €777

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A garden with flowering plants and shrubs in front of a stone building with a tiled roof at Middle Farm Annex in Long Bredy
1 of 40
5
Long Bredy, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    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


for 7 nights From €609

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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
Offer
1 of 25
5
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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
  • Dishwasher

  • €48 off - Fri 7th Aug to 28th Aug 2026


for 7 nights From €809

Last booked yesterday
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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
1 of 14
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • 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


for 7 nights From €894

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A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
1 of 45
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • 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


for 7 nights From €567

Last booked yesterday
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Front exterior of a brick house with white-framed windows and door and garden shrubs with black chairs and table outside at Splash in Weymouth
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. Near beach and pub. Smart TV. Near harbour. Dishwasher. Dorchester 8.6 miles; Bridport 19.4 miles. (Ref. 1154894)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From €799

Last booked 2 days ago
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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
1 of 32
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • 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


for 7 nights From €597

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Front entrance of Bay View Hotel with brick buildings and ivy on walls in Weymouth
1 of 49
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

One @ No36 is a delightful duplex apartment with the beach on your doorstep, with the convenience of off-road parking, in Weymouth, Dorset. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162201)

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


for 7 nights From €892

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A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth
1 of 29
5
Nottington near Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A quaint stone-built cottage resting on the outskirts of Weymouth. Open-plan living. Off-road parking. WiFi. Dorchester 6.4 miles; Fortuneswell 8.2 miles. (Ref. 1061544)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Washing machine


for 7 nights From €634

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
1 of 57
5
Weymouth, Dorset, DT4
  • Sleeps13
  • Bedrooms6
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • Sky TV


for 7 nights From €2469

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A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
1 of 31
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)

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


for 7 nights From €860

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A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
1 of 17
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

An immaculate second-floor apartment resting in the centre of Weymouth. Marina views. Open-plan living room. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059264)

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


for 7 nights From €701

Last booked 2 days ago
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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
1 of 22
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • 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


for 7 nights From €785

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A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
1 of 27
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From €753

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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
1 of 18
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

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

  • Wi-fi
  • Dishwasher


for 7 nights From €590

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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
1 of 18
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • 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


for 7 nights From €714

Last booked yesterday
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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
1 of 31
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From €693

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A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
Offer
1 of 46
5
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)

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

  • €257 off - Fri 21st Aug to 28th Aug 2026


for 7 nights From €1380

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 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!