Your search returned 61 cottages.
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- Sleeps4
- Bedrooms2
- PetsNo
St. (Ref. 994677)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £612
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- Sleeps6
- Bedrooms3
- PetsNo
Three bedrooms on Portland, moments from Chesil beach. (Ref. 994701)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £628
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- Sleeps4
- Bedrooms2
- PetsNo
Manhattan Beach is an apartment with a balcony with sunning sea and marina vistas, on the edge of the village of Castletown, Isle of Portland, in Dorset. (Ref. 1161472)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £596
Secure your holiday with a 30% deposit* Book now -
- Sleeps7
- Bedrooms4
- PetsNo
A spacious, three-storey house settled in Castletown, Portland, Dorset. (Ref. 1107230)
- Wi-fi
- Ground floor bedroom
- Dishwasher
7 nights from £923
Secure your holiday with a 30% deposit* Book now -
- Sleeps5
- Bedrooms3
- PetsYes
A delightful, mid-terrace home just moments from the beach in the village of Wyke Regis, Weymouth. (Ref. 1071852)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £642
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- Sleeps6
- Bedrooms3
- PetsYes
An enticing, semi-detached house sitting in Wyke Regis, Dorset. (Ref. 1097679)
- Wi-fi
- Off-road parking
7 nights from £779
Secure your holiday with a 30% deposit* Book now -
- Sleeps5
- Bedrooms3
- PetsYes
A charming cottage based in the village of Wyke Regis, Dorset. (Ref. 1121449)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £631
Secure your holiday with a 30% deposit* Book now -
- Sleeps8
- Bedrooms4
- PetsYes
Modern and comfortable holiday house for up to 8 people in the Isle of Portland. (Ref. 994310)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
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5% off - Tue 4th Feb to 20th Dec 2025
7 nights from £939
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- Sleeps6
- Bedrooms3
- PetsYes
33 High Street is a well-positioned, three-bedroom home resting in Fortuneswell, Dorset. (Ref. 1138399)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £600
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- Sleeps8
- Bedrooms4
- PetsNo
Detached, large and modern house for large group of friends or big family. (Ref. 994499)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £714
Secure your holiday with a 30% deposit* Book now
Our properties on the wonderful Isle of Portland range from modern contemporary lodges overlooking the sea to stunning harbourside properties with unrivalled sea views, just a stone’s throw from the beautiful Jurassic Coast.
Portland itself offers arguably the best sailing and windsurfing waters in the world, equipped with an abundance of rare wildlife, miles of stunning coastal walks and a beautiful marina to facilitate great fishing trips. Portland also plays host to beautiful beaches, some of which are dog-friendly all year round, fantastic pubs and some of the best cream teas in the whole of Dorset.
Portland Holiday Cottages
Our Portland holiday cottages are equally perfect for those wishing to enjoy the great outdoors, as well as those wishing to cosy up with stunning views right outside their cottage windows.
Our cottages sleep parties of all sizes, as well as many accommodating dogs and young children. Stay in the heart of Portland itself in a lovely village like Easton, or stay in the surrounding area to bask in the beauty of the Dorset coast.
Places to visit near Portland
If you're looking to venture outside of Portland during your stay, then you won't be short for choice. With many other Dorset favourites just a short drive away, you can explore the likes of Chesil Beach and the Jurassic Coast in a day. Locations such as Abbotsbury, Osmington, West Bexington, Chesil Beach, Southwell, West Lulworth and Weymouth are just as beautiful as Portland and offer all sorts of different attractions and days out.
Start your Portland adventure today by chatting to one of our helpful travel experts or continue browsing our secure website.