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 347 cottages
- Sleeps12
- Bedrooms6
- PetsNo
Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £1290
- 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
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
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 £872
- 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 £1052
- 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
- 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
- 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 £663
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
- Sleeps7
- Bedrooms4
- PetsNo
This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £706
- Sleeps4
- Bedrooms2
- PetsNo
Contemporary barn conversion, close to the Dorset coast. Secluded garden. Solid oak flooring. Five minute drive to Weymouth. (Ref. 994207)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £683
- 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
- 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
- Sleeps2
- Bedrooms1
- PetsYes
A quaint stone-built cottage resting on the outskirts of Weymouth. Open-plan living. Off-road parking. WiFi. Dorchester 6.4 miles; Fortuneswell 8.2 miles. (Ref. 1061544)
- Wi-fi
- Off-road parking
- Electric vehicle charging
- Ground floor bedroom
- Washing machine
7 nights from £534
- Sleeps8
- Bedrooms4
- PetsNo
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 £1176
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 well-presented, ground-floor apartment in Weymouth, Dorset. Open-plan. Close to beach. Near an AONB. Ground-floor living. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1126298)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £448
- 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
Offer
- Sleeps13
- Bedrooms6
- PetsNo
Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
- Sky TV
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20% off - Fri 27th Jun to 4th Jul 2025
7 nights from £2124
- 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
- Sleeps4
- Bedrooms2
- PetsNo
A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £666
- Sleeps4
- Bedrooms2
- PetsYes
An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £461
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.