Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 429 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Modern one level apartment. Sitting room, with balcony and beautiful sea views. Short walk to the beach and a causal walk to the town centre. Wifi. (Ref. 994505)

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

7 nights from £597

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A lovely two-bedroom house resting in Weymouth, Dorset. Family-friendly. Enclosed garden. Near a beach. Pet-friendly. Dorchester 6.7 miles; Bridport 19.6 miles. (Ref. 1120462)

  • Wi-fi
  • Washing machine

7 nights from £503

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Lyme View, delightful coastal property resting in Fortuneswell on the Isle of Portland, Dorset. Close to a beach. Garden. Pet friendly. Close to a shop and a pub. Weymouth 5.2 miles; Abbotsbury 11.9 miles; Dorchester 12.8 miles. (Ref. 1135049)

  • Wi-fi
  • Electric vehicle charging
  • Washing machine

7 nights from £695

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A stunning terraced nestled in the large village of Maiden Newton in Dorset. Woodburning stove. Riverside views. Eco-friendly. West Bay 12.4 miles; Weymouth 17 miles; Lyme Regis 22.4 miles. (Ref. 1070251)

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

7 nights from £774

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

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

7 nights from £680

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. Beach 1 mile. Harbour, shop and pub 5 min. Welcomes one dog. Poole 33 miles. (Ref. 1058438)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £633

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.4

    Good

  • Sykes rating

Lovely 4 bedroom house in gated area. Close to Weymouth harbour. Secure gated parking for one car. Welcomes two dogs. WiFi. (Ref. 994213)

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

7 nights from £815

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This homely holiday cottage rests in Wyke Regis in Weymouth in Dorset. Pet-friendly. Nearby beach. Ideal for families. Isle of Portland 4.7 miles; Dorchester 9.4 miles; Bridport 18 miles. (Ref. 1050977)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Baby-friendly

7 nights from £698

  • 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
  • 20% off - Fri 1st Aug to 29th Aug 2025

7 nights from £621

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A thatched end-terrace property, resting within a central location in Burton Bradstock. Off-road parking. Pet-friendly. WiFi. Weymouth 15 miles; Dorchester 16 miles. (Ref. 999154)

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

7 nights from £734

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Situated in a stunning loaction overlooking hills in Dorset. Ground floor accommodation with doors from lounge opening onto large garden. Welcomes two pets. (Ref. 994654)

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

7 nights from £865

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1

    Good

  • Sykes rating

2 Bedroom Apartment with beach views in West Bay. Central Location, close to beach and Harbour. (Ref. 994311)

  • Wi-fi
  • Off-road parking

7 nights from £536

  • Sleeps8
  • Bedrooms5
  • PetsYes

    4.1

    Good

  • Sykes rating

Full of Character thatched cottage just outside Burton Bradstock. Sleeps 8. Shower room and bathroom. Enclosed garden. Wood burning stove (winter months). Parking for 3 cars. (Ref. 994004)

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

7 nights from £741

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A stylish and contemporary period home near Brewers Quay, Weymouth. Stylish. Close to beach. Courtyard with furniture. Close to local amenities. Dorchester 8.4 miles; Bridport 22.1 miles. (Ref. 1109892)

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

7 nights from £687

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming holiday home resting near Shipton Bradstock, Dorset. Dog-friendly. Woodburing stove. Close to beach. Bridport 2.7 miles; Dorchester 13.7 miles; Weymouth 19.8 miles; Yeovil 20.7 miles. (Ref. 1074488)

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

7 nights from £798

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A lovely two-bedroom bungalow resting in Preston, Dorset. Dog-friendly. Off-road parking. Private garden. Close to amenities. Weymouth 3.4 mile. (Ref. 1106680)

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

7 nights from £574

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4

    Good

  • Sykes rating

A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. Open-plan living space. Private parking. Close to the coast. Chickerell 3 miles; Dorchester 8.3 miles; Swanage 28.9 miles. (Ref. 1111030)

  • Wi-fi
  • Dishwasher

7 nights from £637

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the scenic coast of Weymouth, Dorset. Open-plan. Views. Parking. Fortuneswell 5.6 miles; Dorchester 7.6 miles; Bridport 19 miles. (Ref. 1060926)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £682

Last booked yesterday
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  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A well-positioned, three-storey home resting in Fortuneswell, Dorset. Sea views. Close to amenities and the beach. Family-friendly. Private decked area. Near AONB. Weymouth 5.3 miles. (Ref. 1120221)

  • Wi-fi
  • Off-road parking

7 nights from £562

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Bright contemporary property perfect groups of guests in the Isle of Portland. Sea views. WiFi. Shop 10 min. Pub 5 min. Beach 5 min. Weymouth 4.9 miles. (Ref. 994754)

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

7 nights from £766