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 346 cottages
- Sleeps2
- Bedrooms1
- PetsNo
Beautiful seafront apartment within the popular resort of Weymouth in Dorset. Incredible sea views. WiFi. Centre of Weymouth. (Ref. 1003083)
- Wi-fi
- Dishwasher
7 nights from £498
- Sleeps2
- Bedrooms1
- PetsNo
Perfect couples retreat with WIFI. Located in The Nothe in Weymouth, surrounded by beauitful walks and moments from the harbour. (Ref. 993912)
- Wi-fi
- Dishwasher
- Washing machine
-
5% off - Sat 26th Jul to 2nd Aug 2025
7 nights from £502
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 charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
7 nights from £874
- 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
- Sleeps2
- Bedrooms1
- PetsNo
A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples. (Ref. 1003545)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £423
- Sleeps2
- Bedrooms1
- PetsNo
Hideaway is a fine, single-storey annex situated in Weymouth, Dorset, with open-plan living, Smart TV, and well-positioned to nearby beaches and amenities. Dorchester 8.8 miles; Bridport 19.5 miles; Bournemouth 38.4 miles. (Ref. 1169910)
- Wi-fi
- Ground floor bedroom
- Baby-friendly
7 nights from £398
- 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
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 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
- 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
- Sleeps2
- Bedrooms1
- PetsYes
A lovely one-bedroom holiday home resting in Weymouth, Dorset. Romantic. Off-road parking. Private garden. Near a beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1092449)
- Wi-fi
- Off-road parking
- Electric vehicle charging
- Dishwasher
- Washing machine
7 nights from £481
- 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
- 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
- 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
- Sleeps4
- Bedrooms2
- PetsYes
Comfortable Spanish style holiday home in Weymouth. Off road parking for two cars. Patio garden with furniture. Sea views. Beach 5 min. Pub and shop 10 min. Dorchester 9 miles. (Ref. 994352)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £644
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
Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £567
- Sleeps4
- Bedrooms2
- PetsYes
Sleeping four in Maltings area of Weymouth, pet friendly. Off road parking. WiFi. Garden. Close to harbour. (Ref. 994596)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £558
- Sleeps4
- Bedrooms2
- PetsYes
Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. One dog welcome. Wifi. Shop and pub 5 min. Beach 10 min. Dorchester 7 miles. (Ref. 994377)
- Wi-fi
- Off-road parking
- Washing machine
- Baby-friendly
7 nights from £581
- 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
-
5% off - Fri 1st Aug to 8th Aug 2025
7 nights from £462
- 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 £468
- Sleeps4
- Bedrooms2
- PetsYes
Stylish renovated ground floor apartment in Weymouth. Town centre a short walk away. WiFi. Welcomes one dog. Pub and shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994763)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £638
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.