Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 423 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    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


for 7 nights $816

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Beautiful apartment, that welcomes one well behaved dog, located on the esplanade, perfect for discovering the delights of Weymouth. With wifi and off-road parking for two small to mediums sized cars. (Ref. 994451)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • $621 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights $1095

  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Three bedroom terraced property in central Weymouth. Open plan living area. (Ref. 1095056)

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


for 7 nights $1028

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Coastguard Lookout is a modern, reverse-level house near a beach in Wyke Regis, Dorset, with off-road parking, Juliet balcony, and underfloor heating. Weymouth 2.5 miles; Dorchester 9.6 miles. (Ref. 1169223)

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


for 7 nights $696

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This charming two-bedroom property resides in Bridport, Dorset. Gas fire. Close to amenities. Pretty views. West Bay 0.6 miles; Lyme Regis 10.8 miles. (Ref. 1114596)

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


for 7 nights $667

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

First floor comfortable apartment sleeping up to 7 people close to the beach in Weymouth. Welcomes two dogs. Shared garden. Beach 2 min. Shop 10 min. Pub 5 min. Dorchester 7.6 miles. (Ref. 994772)

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


for 7 nights $793

  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Comfortable renovated cottage with rear garden and close to the town centre. Garden with furniture. Pub 5 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994191)

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


for 7 nights $807

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Modern 3 Storey house. Close to the Harbour, Newton’s Cove and Brewers Quay. WIFI. Parking for one car. 5 minutes to local shop. 15 minute walk to town centre. (Ref. 993939)

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


for 7 nights $1010

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Detached, large and modern house for large group of friends or big family. WiFi. Garden with enclosed patio. Parking for 2 cars. Shop and pub 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994499)

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


for 7 nights $938

  • Sleeps10
  • Bedrooms4
  • PetsNo

    4.4

    Good

  • Sykes rating

Electronically gated property. Gated parking for three cars. Sleeps 10. Two min walk to harbour and amenities. (Ref. 994443)

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


for 7 nights $1820

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A desirable second-floor apartment close to West Bay in the heart of Dorset. Flexible accommodation. 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. 1106615)

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


for 7 nights $1015

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

  • Wi-fi
  • Washing machine


for 7 nights $682

  • 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


for 7 nights $1087

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Situated in a gated complex near Weymouth harbour. WiFi. Parking. Close to bars and restaurants. (Ref. 994560)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • $344 off - Sat 20th Dec to 27th Dec 2025

  • $325 off - Sat 27th Dec 2025 to 3rd Jan 2026


for 7 nights $964

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    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


for 7 nights $675

  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • Sykes rating

Mutiny House is situated in a harbourside location in Weymouth. Perfect for a family or group of friends. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994414)

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


for 7 nights $1024

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    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


for 7 nights $833

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

A bright and airy lodge resting in Osmington near Preston, Dorset. Open-plan. Close to beach. Pet-friendly. Weymouth 5.4 miles; Poole 23.4 miles; Bournemouth 29.1 miles. (Ref. 1093891)

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


for 7 nights $960

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)

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


for 7 nights $776

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3

    Good

  • Sykes rating

This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. Sea views. Elegant décor. Close to amenities. Dorchester 7.5 miles; Bridport 19.4 miles. (Ref. 1034440)

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


for 7 nights $774