Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 429 cottages

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  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.2

    Good

  • Sykes rating

The Old Portland Courthouse is spacious, comfortable luxury holiday home. Sleeps 8 people. Wifi. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994487)

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

7 nights from €1387

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A sympathetically converted barn on the outskirts of Uploders near Bridport in Devon. Open-plan. Stylish. Woodburning stove. Uploders 0.9 miles; Bridport 2.8 miles; West Bay 4.2 miles Lyme Regis 13.3 miles. (Ref. 1106581)

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

7 nights from €775

  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. Patio with furniture. Close to amenities. Smart TV. Dorchester 8.2 miles; Bridport 18.7 miles. (Ref. 1144645)

  • Wi-fi
  • Baby-friendly

7 nights from €633

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Excellent period apartment in Weymouth close to the esplanade. Two en-suite shower rooms and three bedrooms. WiFi. Enclosed patio area. Beach 1 min away. (Ref. 993988)

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

7 nights from €1230

  • 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 €951

  • 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 €698

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.6

    Outstanding

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A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples. (Ref. 1003545)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €499

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. Near to shops and town centre. Beach 10 minutes away. WiFi. Dorchester 8.5 miles. (Ref. 994072)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €608

  • 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 €720

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Stylishly renovated bungalow in Burton Bradstock. Off road parking for 2 cars. Wi-Fi. Large open plan family kitchen / dining area / sitting room. (Ref. 994537)

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

7 nights from €845

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. En-suite master bedroom. Beach 1 mile. Dorchester 9 miles. (Ref. 994201)

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

7 nights from €740

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A charming second-floor apartment in the heart of West Bay in Dorset. Spacious, Lift access. WiFi. Open-plan. Harbour views. West Bay 0.1 miles; Bridport 2 miles; Seatown 5.3 miles; Lyme Regis 11.4 miles. (Ref. 1106414)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €874

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

2-minute walk to Sandsfoot beach and the South West Coast path. Uninterrupted sea views to Portland and beyond, sleep 5, parking. (Ref. 994582)

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

7 nights from €839

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Comfortable family seaside holiday home in Weymouth. Two dogs welcome. Rear garden. Wifi. Beach 10 min. Shop and pub 5 min. Isle of Portland 8 miles. (Ref. 994187)

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

7 nights from €918

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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

7 nights from €841

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Tucked in a quiet location in Weymouth, The Pines is a modern holiday home for families or couples. Welcomes two dogs. Pub and shop 10 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994549)

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

7 nights from €756

  • 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 €845

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

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

7 nights from €841

  • 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 €618

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 9 miles. (Ref. 994277)

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

7 nights from €893