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 354 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
  • PetsNo

    4.8

    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)

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

7 nights from $768

  • 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 $639

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

    4.7

    Outstanding

  • 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 $942

Last booked 2 days ago
See more details
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

2-minute walk to Sandsfoot beach and the South West Coast path. Uninterrupted sea views to Portland and beyond, sleep 5, parking. (Ref. 994582)

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

7 nights from $885

  • 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 $726

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

    4.0

    Good

  • Sykes rating

Perfectly located on the harbour side in the heart of Weymouth. Watch the boats sail by and the daily catch being landed. (Ref. 994172)

  • Wi-fi
  • Washing machine

7 nights from $691

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

    4.5

    Outstanding

  • 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 $622

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. Romantic. Near a beach. Pet-free. Close to amenities. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1114655)

  • Wi-fi

7 nights from $662

Last booked yesterday
See more details
  • 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 $907

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Traditional Portland Cottage. Beautiful scenery walks. Close to pubs. (Ref. 993922)

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

7 nights from $641

Last booked yesterday
See more details
  • 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 $707

Last booked 2 days ago
See more details
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A romantic, ground-floor apartment sitting in Weymouth, Dorset. Open-plan. Close to amenities and beach. WiFi. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1102992)

  • Wi-fi
  • Ground floor bedroom

7 nights from $574

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

    4.1

    Good

  • Sykes rating

Harbourside first floor apartment with balcony. Centrally located for all bars and restaurants. WiFi. Sleeps 4. (Ref. 994482)

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

7 nights from $819

  • 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 $772

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    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

7 nights from $620

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Modern and beautiful cottage in the heart of Weymouth. Close to town centre. Wifi. Parking for two cars. Landscaped garden with patio. Shop and pub 5 min. Bridport 22.5 miles. (Ref. 994369)

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

7 nights from $692

  • 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 $1073

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)

  • Dishwasher

7 nights from $717

  • Sleeps5
  • Bedrooms3
  • PetsYes

    3.6

    Good

  • Sykes rating

Neptune cottage situated in the Isle of Portland is very cosy and comfortable. Perfect for dog walks. Beach 2 min. Welcomes two dogs. Pub 5 min, shop 10 min. Weymouth 5 miles. (Ref. 994425)

  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from $715

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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

7 nights from $768

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