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 423 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)
  • Guest Rated (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • 2 Guests
  • 1 Bedroom
  • Pets Yes

    4.8

    Sykes Rating

Trinity Lodge is a striking rural holiday home with great attention to detail, within the Dorset National Landscape, in Goodmanstone, near Cerne Abbas. Dorchester 5.3 miles; Weymouth 14 miles; Sherborne 14.3 miles; Yeovil 17.4 miles. (Ref. 1149594)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from $558

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.8

    Sykes Rating

A lovely two-bedroom house resting in Weymouth, Dorset. Family-friendly. Enclosed garden. Near a beach. Pet-friendly. Dorchester 6.7 miles; Bridport 19.6 miles. (Ref. 1120462)

  • Wi-fi
  • Washing machine

7 nights from $610

7 nights from $696

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. Near beach and pub. Smart TV. Near harbour. Dishwasher. Dorchester 8.6 miles; Bridport 19.4 miles. (Ref. 1154894)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from $818

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.5

    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 $817

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.7

    Sykes Rating

Bright contemporary property perfect groups of guests in the Isle of Portland. Sea views. WiFi. Shop 10 min. Pub 5 min. Beach 5 min. Weymouth 4.9 miles. (Ref. 994754)

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

7 nights from $962

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    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 $760

Last booked 2 days ago
See more details

7 nights from $784

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.5

    Sykes Rating

An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. WiFi. Views over the marina. Off-road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059266)

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

7 nights from $781

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

Stylish renovated ground floor apartment in Weymouth. Town centre a short walk away. WiFi. Welcomes one dog. Pub and shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994763)

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

7 nights from $796

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    Sykes Rating

Upper ground floor apartment in the Admiral’s Quarter development. Partial sea views from the full length windows in the sitting rooms. Modern furnishings. Perfect for a family holiday exploring the delights of Weymouth. Wifi. (Ref. 994438)

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

7 nights from $746

Last booked yesterday
See more details
  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.7

    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

7 nights from $815

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    Sykes Rating

Central location of West Bay, 1st floor apartment. Two bedrooms. Harbour views. Central location. Balcony over harbour. Beach few moments walk from property. Nearby bars and restaurants. (Ref. 994014)

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

7 nights from $804

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    Sykes Rating

A ground-floor apartment resting in West Bay, Dorset. Sea view. Close to a beach. Close to the town centre. Charmouth 8.5 miles; Lyme Regis 11.3 miles; Weymouth 18.2 miles. (Ref. 1106378)

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

7 nights from $885

  • 8 Guests
  • 4 Bedrooms
  • Pets No

    4.9

    Sykes Rating

This charming, four-bedroom holiday home rests in Weymouth, Dorset. Over three floors. Open plan. Off-road parking. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1043677)

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

7 nights from $1479

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)

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

7 nights from $617

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.7

    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 $788

  • 5 Guests
  • 2 Bedrooms
  • Pets Yes

    4.5

    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 $796

  • 10 Guests
  • 4 Bedrooms
  • Pets No

    4.3

    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

7 nights from $1680

  • 7 Guests
  • 3 Bedrooms
  • Pets Yes

    4.7

    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

7 nights from $747