Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 440 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Modern and spacious cottage for couples or family in the Isle of Portland. Enclosed garden. Welcomes one dog. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994497)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €746

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

St. John’s View is a modern holiday home in the Isle of Portland with sea views. Over lower ground floor and ground floor. Shop, pub, beach 5 min. Weymouth 4.6 miles. (Ref. 994677)

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


for 7 nights From €744

  • Sleeps15
  • Bedrooms6
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. Dorchester 7.8 miles; Bridport 19.9 miles. (Ref. 1105510)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room
  • 15% off - Mon 13th Jul to 31st Dec 2026


for 7 nights From €1916

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Seahorse Cottage, a delightful stone terraced cottage near Old Harbour in Weymouth, Dorset, boasts a garden, a nearby beach and amenities, and allows pets. Dorchester 7 miles. (Ref. 1191297)

  • Pets go free
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €604

Last booked today
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.3

    Good

  • Sykes rating

Situated in the beautiful Bowleaze Cove area of Weymouth, just seconds from a beach is this enchanting holiday home. (Ref. 994020)

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


for 7 nights From €1017

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Pebbles Foxglove Way is a charming, two-bedroom holiday home resting near West Bay in Dorset. In an AONB. Off-road parking. Enclosed garden. Smart TV. Bridport 1.5 miles; Lyme Regis 10.9 miles. (Ref. 1015390)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine
  • Sky TV


for 7 nights From €970

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.3

    Good

  • Sykes rating

The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. Off-road parking. Open-plan. Garden. Dorchester 6.1 miles; Abbotsbury 9.8 miles; Bridport 19.3 miles. (Ref. 1149531)

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


for 7 nights From €594

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4

    Good

  • Sykes rating

Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. Woodburning stove. Pet-friendly. Near shop and pub. Dorchester 8.4 miles; Bridport 18.9 miles. (Ref. 1141828)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From €599

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

The Old Dairy is Travellers Rests’ largest stone-built cottage, a converted farm building made for relaxed stays with families, groups and dogs. West Bay 4.7 miles; Lyme Regis 13.8 miles; Weymouth 17.7 miles. (Ref. 1099459)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From €546

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From €839

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Tourist Board 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
  • Baby-friendly


for 7 nights From €710

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Alice's Cottage is a characterful, thatched cottage situated in Burton Bradstock, Dorset. Pet-friendly. Amenities and beach nearby. Lawned garden. Bridport 3.3 miles; Weymouth 15.4 miles. (Ref. 1144638)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From €769

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.6

    Outstanding

  • 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


for 7 nights From €1414

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

A traditional, thatched cottage nestled in Burton Bradstock, close to Dorset's Jurassic Coast. Ideal for families. Pet-friendly. Bridport 2.9 miles; Weymouth 15.8 miles. (Ref. 1135014)

  • Pets go free
  • Wi-fi
  • Washing machine


for 7 nights From €559

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5

    Outstanding

  • Sykes rating

All second floor. Two bedrooms: 1 x double bed with en-suite shower, basin and WC, 1 x twin single. Bathroom with bath, basin and WC. Open plan living area with kitchen, dining area and sitting area. (Ref. 994293)

  • Wi-fi


for 7 nights From €770

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Stone three bedroom cottage near Bridport. Dog friendly. Lawned garden, BBQ/Fire Bowl. . Sleep 6. (Ref. 994548)

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


for 7 nights From €1036

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A well-presented property nestled in the heart of Weymouth, Dorset. Roadside parking. Enclosed patio. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1134491)

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


for 7 nights From €687

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

An outstanding detached house resting within the village of Burton Bradstock, Dorset. Pet-friendly. Woodburning stove. Near a beach. Weymouth 16 miles; Dorchester 16.1 miles. (Ref. 1021187)

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


for 7 nights From €1206