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 343 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
  • Sleeps3
  • Bedrooms2
  • PetsYes

    3.9

    Good

  • Sykes rating

A charming thatched roof character cottage resting in the village of Osmington, Dorset. Off-road parking. Open-plan living. WiFi. Close to pub. Weymouth 4.4 miles; Dorchester 5.4 miles. (Ref. 1064960)

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

7 nights from £456

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

18 Chamberlaine Road is a lovely and welcoming abode, near a beach, situated in the heart of Weymouth, Dorset, only a short walk to a local shop and pub. Dorchester 9.3 miles; Bridport 17.8 miles. (Ref. 1161457)

  • Wi-fi
  • Washing machine

7 nights from £472

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Mermaid Cottage is a delightful, contemporary cottage close to a beach and amenities, in the village of Wakeham, on the Isle of Portland, in Dorset. Weymouth 7.2 miles; Dorchester 14.2 miles. (Ref. 1143548)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • 15% off - Fri 1st Nov to 22nd Dec 2024

7 nights from £532

  • Sleeps15
  • Bedrooms6
  • PetsYes
  • 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)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £1498

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Good

  • Sykes rating

Crows Nest is a charming, reverse-level cottage in the seaside village of Fortuneswell, Dorset on the Jurassic Coast and close to amenities and a beach. Weymouth 5.7 miles; Dorchester 12.7 miles; West Bay 20.3 miles. (Ref. 1162358)

  • Wi-fi
  • Ground floor bedroom
  • 10% off - Fri 20th Dec 2024 to 3rd Jan 2025

7 nights from £515

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

74 Reap Lane is a lovely home resting near the village of Weston, on the Isle of Portland in Dorset. Near beach and pub. Pet-friendly. Off-road parking. Fortuneswell 2.2 miles; Weymouth 7.8 miles; Dorchester 14.8 miles. (Ref. 1158199)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £460

  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. Dorchester 8.5 miles; Bridport 19.3 miles. (Ref. 1140944)

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

7 nights from £599

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Manhattan Beach is an apartment with a balcony with sunning sea and marina vistas, on the edge of the village of Castletown, Isle of Portland, in Dorset. Portland 2.2 miles; Weymouth 5.5 miles; Dorchester 12.5 miles. (Ref. 1161472)

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

7 nights from £596

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

Home From Home is a delightful cottage nestled in the village of Fortuneswell in Dorset, Isle of Portland and is pet-friendly and near the beach. Weymouth 5.5 miles (Ref. 1158103)

  • Wi-fi
  • Washing machine

7 nights from £524

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • 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 £620

Last booked yesterday
See more details
  • 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 £499

  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.9

    Good

  • Sykes rating

Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. Close to beach, shops and amenities. Dishwasher. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1139963)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £614

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1

    Good

  • 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 £495

  • 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 £611

  • Sleeps10
  • Bedrooms5
  • PetsYes
  • Sykes rating

26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. Smart TV. Pet-friendly. Sea views. Close to amenities. Dorchester 7.9 miles; Bridport 20.6 miles. (Ref. 1118900)

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

7 nights from £1252

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. Near coast. Woodburning stove. Open-plan. Near pub. Dorchester 8.7 miles; Bridport 19.4 miles. (Ref. 1159836)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £700

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Dolly Dream is a well-appointed duplex apartment close to a beach and shops, resting in the bustling town of Weymouth in Dorset. Dorchester 6.8 miles; Bridport 19.7 miles. (Ref. 1152003)

  • Wi-fi
  • Washing machine

7 nights from £760

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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

7 nights from £631

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.3

    Good

  • 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

7 nights from £1177

  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

An attractive, terraced, three-storey house near Chesil Beach in Fortuneswell, Dorset. Off-road parking. Dog-friendly. Enclosed terrace. Smart TV. Bedroom with en-suite. Weymouth 4.6 miles. (Ref. 1091335)

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

7 nights from £631

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