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 343 cottages
- 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 $668
- 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 $722
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, 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 $722
- 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 $676
- 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 $644
- 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 $1171
- 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 $952
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
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 $674
- Sleeps4
- Bedrooms2
- PetsYes
A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from $952
- 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 $849
- 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
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5% off - Fri 1st Aug to 8th Aug 2025
7 nights from $625
- 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 $869
- 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 $1103
- 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 $633
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 Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. Dorchester 8.5 miles; Bridport 20.5 miles; Poole 32.2 miles. (Ref. 1107935)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from $690
- 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 $632
- Sleeps4
- Bedrooms2
- PetsYes
A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $1211
- Sleeps4
- Bedrooms2
- PetsYes
A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Washing machine
7 nights from $864
- Sleeps4
- Bedrooms2
- PetsYes
Sleeping four near harbourside in Weymouth. Welcome two dogs. Pubs, restaurants and harbour 5 mins walk. (Ref. 994584)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from $802
- 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 $857
Please find below a selection of self catering holiday cottages to rent in or near Chiswell On Portland.