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 354 cottages
- Sleeps6
- Bedrooms3
- PetsNo
Located in the coastal village of West Lulworth is this stunning converted chapel. Stylish and contemporary interior. WiFi. Woodburning stove. Wareham 8.9 miles; Dorchester 12.7 miles; Weymouth 20.7 miles. (Ref. 1055781)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from $1458
- 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 $772
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- Sleeps4
- Bedrooms2
- PetsYes
Fisherman's Cottage, King Street, is a charming cottage resting in Fortuneswell, Dorset. Close to a shop and a pub. Close to a beach. Woodburning stove. Weymouth 5.4 miles; Dorchester 12.4 miles. (Ref. 1152166)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $639
- 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 $942
- Sleeps7
- Bedrooms3
- PetsNo
A well-positioned, three-storey home resting in Fortuneswell, Dorset. Sea views. Close to amenities and the beach. Family-friendly. Private decked area. Near AONB. Weymouth 5.3 miles. (Ref. 1120221)
- Wi-fi
- Off-road parking
7 nights from $796
- 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 $646
- 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 $686
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- 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 $603
- 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 $620
- 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 $1073
- Sleeps4
- Bedrooms2
- PetsNo
A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)
- Wi-fi
- Swimming pool
- Dishwasher
- Washing machine
7 nights from $697
- 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 $767
- Sleeps5
- Bedrooms3
- PetsNo
2-minute walk to Sandsfoot beach and the South West Coast path. Uninterrupted sea views to Portland and beyond, sleep 5, parking. (Ref. 994582)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $885
- 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 $768
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- 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 $622
- Sleeps4
- Bedrooms2
- PetsNo
Traditional Portland Cottage. Beautiful scenery walks. Close to pubs. (Ref. 993922)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $641
- Sleeps4
- Bedrooms2
- PetsNo
An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. WiFi. Views over the marina. Off-road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059266)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $819
- Sleeps6
- Bedrooms3
- PetsNo
Modern 3 Storey house. Close to the Harbour, Newton’s Cove and Brewers Quay. WIFI. Parking for one car. 5 minutes to local shop. 15 minute walk to town centre. (Ref. 993939)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $942
- Sleeps5
- Bedrooms3
- PetsNo
A delightful, three bed property nestled in the heart of Weymouth, Dorset. Enclosed courtyard. Washing machine. Smart TV. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1132346)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from $607
- Sleeps6
- Bedrooms4
- PetsNo
Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. Original features. Close to amenities, attractions and the harbour. Balcony. Dorchester 8.5 miles; West Lulworth 15.3 miles. (Ref. 1137640)
- Wi-fi
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from $928
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.