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.
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.
Your Portland, Dorset search returned 358 cottages
- Sleeps8
- Bedrooms4
- PetsYes
A beautifully presented townhouse resting in the popular seaside town of Weymouth, close to Newton’s Cove, Dorset. Close to amenities. Garden with furniture. Off-road parking. Dorchester 8.6 miles; West Lulworth 15.6 miles (Ref. 1066546)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
- Sky TV
7 nights from €1055
- 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 €566
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- Sleeps4
- Bedrooms2
- PetsYes
Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. Accepts one dog. Pub and shop 5 min. Beach 5 min. Bridport 23 miles. (Ref. 994321)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €584
- Sleeps4
- Bedrooms2
- PetsNo
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 €569
- Sleeps4
- Bedrooms2
- PetsNo
A well-presented apartment with views over Portland Marina in Castletown, Dorset. Balcony. En-suite. Beach nearby. Portland 2.1 miles; Weymouth 5 miles. (Ref. 1136982)
- Wi-fi
- Washing machine
7 nights from €608
- Sleeps4
- Bedrooms2
- PetsNo
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 €811
- 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 €1338
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- 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 €772
- Sleeps6
- Bedrooms3
- PetsNo
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 €707
- Sleeps6
- Bedrooms3
- PetsNo
The Old Police Station is a fantastic house residing in Fortuneswell, Dorset. WiFi. Open-plan. Family-friendly. Parking. Enclosed patio. Near the beach and coast. Sea views. Easton 1.6 miles; Grove 2 miles; Weymouth 4.7 miles. (Ref. 1082042)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €1111
- Sleeps5
- Bedrooms3
- PetsNo
A wonderful, end-terrace house perched on the coast in Wyke Regis, Dorset. Sea views. Electric fire. Weymouth 2.6 miles; Dorchester 10.2 miles. (Ref. 1091445)
- Wi-fi
- Off-road parking
- Washing machine
- Baby-friendly
7 nights from €829
- Sleeps4
- Bedrooms2
- PetsYes
A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)
- Dishwasher
7 nights from €656
- Sleeps4
- Bedrooms3
- PetsYes
Chapelhay Cottage is a lovely, terraced cottage nestled into the seaside town of Weymouth, Dorset. Close shop and a pub. Close to a beach. Jurassic Coast. Portland 5.9 miles; Dorchester 8.4 miles; Lyme Regis 28.3 miles. (Ref. 1131030)
- Wi-fi
- Ground floor bedroom
- Dishwasher
7 nights from €686
- Sleeps5
- Bedrooms3
- PetsYes
A stone Fisherman's cottage on Portland, WIFI, ideal location for exploring Portland, sail at the National Sailing academy and the Jurassic Coast. (Ref. 993918)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €702
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- Sleeps4
- Bedrooms1
- PetsNo
Centrally located, near to Weymouth harbour. Sleeps 4. Patio and off road parking. Close to bars and restaurants. (Ref. 994563)
- Wi-fi
- Off-road parking
- Washing machine
7 nights from €481
- 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 €841
- Sleeps6
- Bedrooms3
- PetsNo
Bright contemporary property perfect groups of guests in the Isle of Portland. Sea views. WiFi. Shop 10 min. Pub 5 min. Beach 5 min. Weymouth 4.9 miles. (Ref. 994754)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Washing machine
7 nights from €862
- 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 €551
- Sleeps2
- Bedrooms1
- PetsNo
A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. Balconies. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1078324)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from €627
- Sleeps6
- Bedrooms3
- PetsNo
A beautifully presented property just moments from Weymouth harbour and Netwon's Cove in Dorset. Near amenities. WiFi. Off-road parking. En-suite. Isle of Portland 6.1 miles; Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1056258)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from €843
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.