Chiswell On Portland Holiday Cottages
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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 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
- 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 €729
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- 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
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
- 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
- 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
- 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 €586
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 €486
- 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
- Sleeps4
- Bedrooms2
- PetsYes
Lyme View, delightful coastal property resting in Fortuneswell on the Isle of Portland, Dorset. Close to a beach. Garden. Pet friendly. Close to a shop and a pub. Weymouth 5.2 miles; Abbotsbury 11.9 miles; Dorchester 12.8 miles. (Ref. 1135049)
- Wi-fi
- Electric vehicle charging
- Washing machine
7 nights from €584
- 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 €761
- 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 €849
- 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 €638
- Sleeps4
- Bedrooms2
- PetsYes
A lovely terraced house resting in a quiet residential area of Weymouth, Dorset. Enclosed garden. Pet-friendly. Near to beach. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1053611)
- Wi-fi
- Off-road parking
- Washing machine
7 nights from €546
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- 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 €555
- Sleeps4
- Bedrooms2
- PetsNo
The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. Close to amenities. Near beach. Enclosed courtyard. Dorchester 7.1 miles; Bridport 19.1 miles. (Ref. 1129331)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from €633
- 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
- Sleeps2
- Bedrooms1
- PetsNo
A characterful one-bedroom property resting in Weymouth, Dorset. Close to amenities and a beach. Near an AONB. Couples retreat. Dorchester 6.8 miles; Bridport 18.3 miles. (Ref. 1125691)
- Wi-fi
7 nights from €360
- 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 €665
- 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
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.