Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 429 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A beautifully presented property located in peaceful village of Burton Bradstock. Off-road parking. Woodburning stove. WiFi. Bridport 2.9 miles; Dorchester 14.4 miles; Weymouth 15.8 miles. (Ref. 1069215)

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

7 nights from $1281

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

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

7 nights from $996

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. One dog welcome. Wifi. Shop and pub 5 min. Beach 10 min. Dorchester 7 miles. (Ref. 994377)

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

7 nights from $743

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This delightful, two-bedroom bungalow rests in Preston, Dorset. Ground-floor living. Enclosed garden. Near an AONB. Weymouth 3.5 miles. (Ref. 1126160)

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

7 nights from $799

  • 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 $824

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A homely, mid-terrace cottage based in Weymouth. Enclosed decking. Smart TV. Beach nearby. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1094925)

  • Wi-fi
  • Off-road parking
  • Baby-friendly

7 nights from $743

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine

7 nights from $716

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 15% off - Fri 6th Jun to 4th Jul 2025

7 nights from $857

  • 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 $903

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A well-positioned, three-storey property resting in Weymouth, Dorset. Sea views. Close to amenities and the beach. Enclosed garden. Elevated position. Dorchester 8.9 miles; Bridport 20.6 miles. (Ref. 1118939)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $790

Last booked 5 hours ago
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Modern, bright apartment with sea views over to Weymouth Bay. Short walk to the beach and a casual stroll to the town centre. Wifi and off-road parking. Great base for exploring Weymouth and the surrounding areas. (Ref. 1098447)

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

7 nights from $880

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2

    Good

  • Sykes rating

Sleeps six in Weymouth, patio garden. Off road parking. 10 mins walk from Weymouth harbour. (Ref. 994586)

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

7 nights from $845

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. Close to amenities and harbour. Pet-free. Garden. Dorchester 8.7 miles; West Lulworth 15.8 miles. (Ref. 1093760)

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

7 nights from $804

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A contemporary and spacious third floor apartment on the Old Harbourside in Weymouth. Secure Private parking. Balcony. WiFi. Dorchester 7 miles; Bridport 17 miles. (Ref. 999829)

  • Wi-fi
  • Off-road parking

7 nights from $859

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming barn conversion on the outskirts of Uploders near Bridport in Dorset. Stylish. Woodburning stove. Open-plan. Great location. Bridport 2.8 miles; West bay 4.2 miles; Lyme Regis 13.3 miles. (Ref. 1106494)

  • Dishwasher
  • Washing machine

7 nights from $670

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A fabulous, reverse-level, four-bedroom home resting in West Bay, Dorset. Sea views. Pet-friendly. Close to amenities and beach. . In AONB. Bridport 2.1 miles; Lyme Regis 11.5 miles. (Ref. 1059577)

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

7 nights from $1841

  • Sleeps5
  • Bedrooms3
  • PetsNo
  • Sykes rating

Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. Weymouth 2.5 miles; Dorchester 10.2 miles; Poole 34.1 miles. (Ref. 1047698)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 5% off - Sat 12th Apr to 30th May 2025

7 nights from $699

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Generous second floor apartment with spectacular sea views. Two bedrooms; one twin and on double. WiFi. 10-minute walk to the town centre. Beach 1 minute away. (Ref. 993990)

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

7 nights from $828

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. Walking distance to town centre. Pub, shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994737)

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

7 nights from $956

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • 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 $758

Last booked 2 days ago
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