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Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 440 cottages

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  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

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

7 nights from £519

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A warm and restful converted annex in West Bay, Dorset. Off-road parking. Close to the coast. Bridport 1.5 miles; Lyme Regis 10.9 miles. (Ref. 1067413)

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

7 nights from £538

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

A characterful, thatched cottage resting in Langton Herring near Chickerell, Dorset. Original features. Close to amenities. Dorset AONB. Pet-friendly. Abbotsbury 4.5 miles; Weymouth 5.8 miles; Portland 9.3 miles; Dorchester 9.7 miles. (Ref. 1123272)

  • Wi-fi
  • Baby-friendly

7 nights from £559

Last booked yesterday
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  • 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 £635

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. Open plan living, en-suite facilities, private patio. Furnished and equipped to a very high standard. Weymouth 3.5 miles. (Ref. 932157)

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

7 nights from £582

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. Very high standard of accommodation with en-suite facilities and vaulted ceiling. Dog-friendly, plenty to see and do in the area. Weymouth 3.5 miles. (Ref. 932158)

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

7 nights from £582

  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A charming, three-bedroom cottage sitting in Chickerell, Dorset. Close to amenities. Enclosed garden. Off-road parking. Weymouth 3.3 miles; Abbotsbury 5.9 miles; Portland 7.2 miles. (Ref. 1086432)

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

7 nights from £607

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1

    Good

  • Sykes rating

Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. Open plan living kitchen diner. (Ref. 1091449)

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

7 nights from £507

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    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 £718

Last booked yesterday
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  • Sleeps9
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • Sykes rating

A beautiful conversion of the Devenish Brewery malthouse, just moments from the harbourside. Sleeps 9, WIFI, stylish curved kitchen. Games Room (Ref. 993976)

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

7 nights from £1143

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • 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
  • £200 off - Fri 26th Jul to 30th Aug 2024

7 nights from £520

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A wonderful stone cottage set in Langton Herring within the beautiful county of Dorset. Close to the coast. Open fire. Pet friendly. Weymouth 5.7 miles; Isle of Portland 9.6 miles; Dorchester 10 miles. (Ref. 1061319)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly
  • Games room
  • £421 off - Fri 20th Dec to 27th Dec 2024

  • £1073 off - Fri 27th Dec 2024 to 3rd Jan 2025

7 nights from £590

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A delightful 3 storey fishermans cottage that has been beautifully restored in the harbour area of Weymouth. (Ref. 993928)

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

7 nights from £557

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  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A spacious, semi-detached house resting in Weymouth, Dorset. Pet-friendly. Off-road parking. Open-plan. Bedroom with en-suite. Enclosed garden. Dorchester 4.7 miles; Bridport 17.2 miles. (Ref. 1105244)

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

7 nights from £781

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Rural retreat for family or couples in quiet village of West Bexington. Two well-behaved dogs welcome. Beach 5 min. Pub 5 min. Farm shop 5 min. Weymouth 13.5 miles. (Ref. 994791)

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

7 nights from £484

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A second-floor apartment resting in Weymouth. Harbour views. WiFi. Garage parking. Dorchester 8.5 miles. (Ref. 1007302)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £533

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  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

This fabulous three-bedroom abode resides in Weymouth, Dorset. Sea glimpses. Smart TV. Open-plan. Near an AONB. Dorchester 7 miles; Bridport 19.5 miles. (Ref. 1125198)

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

7 nights from £669

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Beautiful and comfortable retreat for couples or family in West Bexington. Garden. Two pets welcome. Beach 5 min. Pub 5 min. Burton Bradstock 4 miles. Weymouth 14 miles. (Ref. 994206)

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

7 nights from £484

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • 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 £612

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A marvellous third-floor penthouse situated overlooking the harbour in Weymouth, Dorset. Underfloor heating. Smart TV. Allocated Off road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059267)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 1st Jun to 31st Aug 2024

7 nights from £623

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!