Chiswell On Portland Holiday Cottages

British Travel Award Winners!
We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.
Your Portland, Dorset search returned 343 cottages
- Sleeps6
- Bedrooms3
- PetsYes
Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £1076
- Sleeps4
- Bedrooms2
- PetsYes
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 £653
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps2
- Bedrooms1
- PetsYes
Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £494
- Sleeps5
- Bedrooms3
- PetsYes
Modern family house located on the edge of Weymouth, with sea views. Short drive to town centre. Welcomes two dogs. Garden. Pub and shop 10 min. Beach 2 min. Bridport 19 miles. (Ref. 994759)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £631
- Sleeps4
- Bedrooms2
- PetsNo
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
- Sleeps6
- Bedrooms3
- PetsYes
Cosy, comfortable and luxurious three storey house in Weymouth. Perfect for families. WiFi. Courtyard. One dog welcome. Pub and shop 5 min. Beach 10 min. Dorchester 8 miles. (Ref. 994606)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £946
- Sleeps5
- Bedrooms3
- PetsYes
A charming cottage based in the village of Wyke Regis, Dorset. Beach nearby. Dishwasher. Electric fire. Wifi. Weymouth 2.1 miles; Dorchester 9.7 miles. (Ref. 1121449)
- Wi-fi
- Off-road parking
- Electric vehicle charging
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £644
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps6
- Bedrooms3
- PetsYes
A contemporary townhouse situated just a stone’s throw from Chesil Beach. Pet-friendly. Three floors. Beach views. Weymouth 4.5 miles. (Ref. 1084822)
- Wi-fi
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £579
- Sleeps4
- Bedrooms2
- PetsNo
Three @ No36, a delightful, second-floor apartment situated in the town of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Smart TV. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162204)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £606
- Sleeps6
- Bedrooms3
- PetsNo
This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £593
- Sleeps6
- Bedrooms3
- PetsYes
Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. Pet-friendly. WiFi. Enclosed garden. (Ref. 1008404)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £581
- Sleeps6
- Bedrooms3
- PetsYes
A lovely three-storey house resting in Weymouth, Dorset. Dog-friendly. Near a beach. Off-road parking. Private garden. Dorchester 8.7 miles; Bridport 19.1 miles. (Ref. 1092302)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £762
- Sleeps6
- Bedrooms3
- PetsYes
An enticing, semi-detached house sitting in Wyke Regis, Dorset. Sea views. Near the beach and coast. Balcony. Weymouth 3.3 miles; Isle of Portland 3.8 miles; Dorchester 10.3 miles. (Ref. 1097679)
- Wi-fi
- Off-road parking
7 nights from £740
- Sleeps4
- Bedrooms2
- PetsYes
A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Washing machine
- Baby-friendly
7 nights from £783
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps4
- Bedrooms2
- PetsNo
A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £698
- Sleeps4
- Bedrooms2
- PetsNo
Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. Near to shops and town centre. Beach 10 minutes away. WiFi. Dorchester 8.5 miles. (Ref. 994072)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £515
- Sleeps7
- Bedrooms3
- PetsYes
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 £737
- Sleeps2
- Bedrooms1
- PetsNo
A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)
- Wi-fi
- Off-road parking
7 nights from £500
- Sleeps2
- Bedrooms1
- PetsNo
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 £476
- Sleeps4
- Bedrooms2
- PetsYes
This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
7 nights from £824
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.