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 346 cottages
- 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
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).
- 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
- Sleeps4
- Bedrooms2
- PetsNo
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 £595
- 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
- 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
- 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
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
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
- 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
- Sleeps6
- Bedrooms3
- PetsYes
Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. Dorchester 9 miles; West Lulworth 15.9 miles (Ref. 1173548)
- Wi-fi
- Dishwasher
- Washing machine
-
15% off - Fri 25th Jul to 22nd Aug 2025
7 nights from £651
- 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
- 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
- Sleeps4
- Bedrooms2
- PetsNo
Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)
- Wi-fi
- Off-road parking
- Dishwasher
7 nights from £641
- Sleeps4
- Bedrooms2
- PetsNo
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 £599
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
- PetsNo
Just a 3-minute walk to the old harbour, town bridge and beach beyond this fully modernised mid terrace cottage includes three beds, three bathrooms and two off-road parking spaces.. Dorchester 8.4 miles; Bridport 18.9 miles. (Ref. 1099795)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £768
- Sleeps4
- Bedrooms2
- PetsNo
Ground Floor modern accommodation. Near to Weymouth Town centre and nature reserve. Perfect for families or couples. Allocated parking. Modern property. WIFI. (Ref. 994034)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £446
- 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
A fabulous three-bedroom holiday home in Wyke Regis, Dorset. Pet-friendly. Sea views. Close to beach and amenities. Open-plan. Contemporary. Weymouth 2.2 miles; Dorchester 9.6 miles. (Ref. 1103441)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £763
- Sleeps6
- Bedrooms3
- PetsNo
A beautiful terraced fisherman’s cottage resting in the coastal town of Weymouth, Dorset. Close to a beach. Close to a pub. TV. Dorchester 8.4 miles; West Bay 18.1 miles, Lyme Regis 32.6 miles. (Ref. 1133009)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £568
- Sleeps4
- Bedrooms2
- PetsNo
One @ No36 is a delightful duplex apartment with the beach on your doorstep, with the convenience of off-road parking, in Weymouth, Dorset. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162201)
- Wi-fi
- Off-road parking
- Dishwasher
7 nights from £713
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.