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.

Chiswell On Portland Holiday Cottages

REFINE SEARCH

Your Portland, Dorset search returned 359 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
  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Garland is a delightful abode resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105442)

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

7 nights from $731

Last booked yesterday
See more details
  • Sleeps5
  • Bedrooms3
  • PetsYes
  • Sykes rating

Norden Cottage is a fine, three-bedroom abode resting in Osmington, Dorset. Woodburning stove. Pet-friendly. Enclosed garden. Close to amenities. Weymouth 4.9 miles. (Ref. 1149647)

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

7 nights from $729

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

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from $609

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. Ground-floor living. Near to shop and pub. En-suite. Dorchester 8.5 miles; Bridport 17.5 miles. (Ref. 1152691)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • 20% off - Fri 29th Mar to 6th Apr 2024

7 nights from $836

  • Sleeps5
  • Bedrooms3
  • PetsYes
  • 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 $709

Last booked yesterday
See more details
  • Sleeps8
  • Bedrooms5
  • PetsYes
  • Sykes rating

Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Large property. Dorchester 7.5 miles; West Bay 17.5 miles. (Ref. 1035186)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $914

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo
  • 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

7 nights from $692

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

Salt Tides is a stylish, three-storey holiday home resting in Weymouth, Dorset. Enclosed courtyard. Pet-friendly. Close to amenities and the beach. Dorchester 8.1 miles; Bridport 18.8 miles. (Ref. 1141124)

  • Wi-fi
  • Dishwasher

7 nights from $1028

  • Sleeps7
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • 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 $789

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

Sunset View is a perfectly-positioned, fifth-floor apartment residing in Castletown, Dorset. Sea views. Close to amenities and the beach. Private balcony. Portland 2.1 miles; Weymouth 5 miles; Dorchester 12.4 miles. (Ref. 1141111)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from $600

Last booked 2 hours ago
See more details
  • Sleeps5
  • Bedrooms3
  • PetsNo
  • Sykes rating

Anchor Cottage is a delightful, terraced home resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Family-friendly. Dorchester 7.6 miles; West Bay 17.8 miles. (Ref. 1150151)

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

7 nights from $677

Last booked 2 days ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Three bedrooms on Portland, moments from Chesil beach. Balcony overlooking sea and coastline. (Ref. 994701)

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

7 nights from $760

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine

7 nights from $691

  • 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 $899

Last booked 2 days ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Chenies is a traditional cottage in the delightful hamlet of Osmington Mills near Preston, Dorset. Sea views. Near a pub. Characterful. Open fire. Preston 2.8 miles; Weymouth 5.9 miles. (Ref. 1149628)

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

7 nights from $651

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Lyme View, delightful coastal property resting in Fortuneswell on the Isle of Portland, Dorset. Close to a beach. Garden. Pet friendly. Close to a shop and a pub. Weymouth 5.2 miles; Abbotsbury 11.9 miles; Dorchester 12.8 miles. (Ref. 1135049)

  • Wi-fi
  • Electric vehicle charging
  • Washing machine

7 nights from $627

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6

    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

7 nights from $880

  • Sleeps8
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming terraced property resting in Fortuneswell, Dorset. Sea views. WiFi. Terrace garden. Pet-friendly. Weymouth 5.2 miles. (Ref. 1035417)

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

7 nights from $701

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A delightful 3 storey fishermans cottage that has been beautifully restored in the harbour area of Weymouth. (Ref. 993928)

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

7 nights from $672

Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.