24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Chesil Cottage Holidays

REFINE SEARCH

Your Chesil Beach, Dorset search returned 437 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • £200 off - Fri 26th Jul to 30th Aug 2024

7 nights from £520

Last booked 3 hours ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Sleeping 4 cosy cottage in Weymouth. Close to harbour and all amenities. Gated development. (Ref. 994605)

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

7 nights from £578

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.0

    Good

  • Sykes rating

A wonderful, newly renovated three-bedroom house resting in Weymouth, Dorset. Pet-friendly. Near a beach. Family-friendly. Enclosed patio. Dorchester 8.8 miles; Bridport 20.9 miles. (Ref. 1094065)

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

7 nights from £680

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Fisherman's Cottage, King Street, is a charming cottage resting in Fortuneswell, Dorset. Close to a shop and a pub. Close to a beach. Woodburning stove. Weymouth 5.4 miles; Dorchester 12.4 miles. (Ref. 1152166)

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

7 nights from £415

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Located in a quiet location in Weymouth, Upsidedown House is a unique and beautiful holiday home. Pub and shop 2 min. Beach 10 min. Dorchester 8.4 miles. (Ref. 994746)

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

7 nights from £849

Last booked 2 days ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4

    Good

  • Sykes rating

A period conversion apartment Bayview Loft is located in an upmarket development in a highly desirable area of Weymouth in Dorset. Renovated early 2023. WiFi. (Ref. 1085793)

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

7 nights from £630

  • 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 £581

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 1st Jun to 31st Aug 2024

7 nights from £676

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. Sea views. Electric fire. Weymouth 2.6 miles; Dorchester 10.2 miles. (Ref. 1091445)

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

7 nights from £709

  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.9

    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 £633

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • 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)

  • Wi-fi
  • Dishwasher

7 nights from £441

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. Allocated parking. WiFi. Close to beach and amenities. Dorchester 8.5 miles; West Lulworth 17.4 miles. (Ref. 1146011)

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

7 nights from £593

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 1st Jun to 31st Aug 2024

7 nights from £676

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • 20% off - Fri 21st Jun to 28th Jun 2024

  • 10% off - Sat 20th Jul to 6th Sep 2024

7 nights from £448

Last booked 2 days ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • 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

7 nights from £612

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2

    Good

  • Sykes rating

This contemporary, three-storey holiday home rests in Weymouth, Dorset. Off-road parking and garage. Enclosed garden. Pet-free. Close to amenities. Dorchester 7.6 miles; Bridport 18.3 miles. (Ref. 1102609)

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

7 nights from £794

  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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

7 nights from £686

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Beautiful and spacious cottage over three floors in Weymouth. Next to the Old Harbour and close to town centre. Beach 1 mile. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994354)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from £489

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £471

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

WiFi. Open fire. Two bedrooms close to Weymouth seafront. Off road parking for two cars. (Ref. 994429)

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

7 nights from £576