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.
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Over 30 years of experience in UK self-catering holidays.
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Your Portland, Dorset search returned 344 cottages
- 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 £1300
- 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 £1177
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
- 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
Offer
- 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
-
5% off - Sun 1st Jun to 30th Jun 2025
7 nights from £1290
- 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
- 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
- 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).
- 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
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
- Sleeps2
- Bedrooms1
- PetsNo
A contemporary second-floor apartment resting on the Weymouth Seafront, Dorset. Open-plan living. Sea views. Close to amenities and beach. Pet-free. Stylish. Dorchester 7.8 miles; Bridport 20.3 miles. (Ref. 1092706)
- Wi-fi
- Dishwasher
7 nights from £636
- 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
7 nights from £2126
- Sleeps5
- Bedrooms3
- PetsYes
A delightful, mid-terrace home just moments from the beach in the village of Wyke Regis, Weymouth. Pet-friendly. WiFi. Off-road parking for one car. Weymouth 2.6 miles; Dorchester 10.2 miles. (Ref. 1071852)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £619
- 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
- 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
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
- PetsNo
A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £714
- 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 £466
- Sleeps5
- Bedrooms2
- PetsNo
Blue Yonder is a cheerful, terrace holiday home resting by the sea in Weymouth, Dorset. Sea views. Ground-floor living. Near beach. Close to pub. Dorchester 7.5 miles; Bridport 20.9 miles. (Ref. 1144628)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £636
- 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
- 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
- PetsYes
An inviting, mid-terrace house perched on the coast in Weymouth, Dorset. Sea views. Off-road parking. Near the beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1082718)
- Wi-fi
- Washing machine
- Baby-friendly
7 nights from £467
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.