Portland Holiday Cottages

Find your perfect Portland holiday cottage including pet-friendly Portland holiday cottages. Whether you are looking for a romantic break or a family holiday, we have a great collection of cottages to choose from.
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St Johns View - Fortuneswell

St Johns View is a contemporary detached house situated in Fortuneswell in Portland in Dorset with sea views. The house can sleep 4 people in a king-size double with en-suite...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £417
Exterior | Jurassica House, Portland
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Jurassica House - Fortuneswell

Jurassica House is part of our Olympic legacy, home to the Swedish sailing team during the sailing events in 2012. A great location for water sports enthusiasts, walkers, cyclists, rock...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £848
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Sunrise Hill - Castletown

Sunrise Hill is an excellent apartment perched on the coast in Castletown, Portland. Hosting one double bedroom, along with a bathroom, this property sleeps up to two guests. There is...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £364
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Neptune Cottage - Fortuneswell

Neptune Cottage is a traditional Portland cottage situated in Fortuneswell, Portland, Dorset and benefits from its location on Chesil Beach. The cottage can sleep 5 people in 1 double, 1...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £444
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The Chesil Lookout - Fortuneswell

The living areas in the property consist of a kitchen with an oven, hob, microwave, fridge, washing machine, tumble dryer, dishwasher, dining room with seating for 12 people and a...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £1326
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Ammonite Cottage - Fortuneswell

Ammonite Cottage is traditional Portland stone cottage on the Isle of Portland, near to Weymouth in Dorset, benefits from two bedrooms and one bathroom and can sleep four people. The...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £400
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Portland View - Portland Bill

Portland View is a two-bedroom apartment located on the Isle of Portland with sea views from the balcony and perfect for those that love walking and the outdoors. With everything...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £450
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Bowman’s Cottage - Wakeham

Charming stone-built cottage scrupulously modernised and located close to Church Ope Cove

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £385
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Boatswain’s Watch - Fortuneswell

Boatswain’s Watch is a lovely semi-detached Victorian cottage resting in Fortuneswell, Dorset. Hosting two bedrooms: one double and one single with a pull-out bed, together sleeping up to four guests....

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £381
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The Old Portland Courthouse - Fortuneswell

The Old Portland Courthouse is a Grade II listed converted house situated in Fortuneswell, Portland in Dorset with antique furnishings and sea views. The house can sleep 8 people in...

Secure your 2022 Dorset Holiday Cottage holiday cottage with just a 30% deposit
  • From £944

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