5 Star Portland Holiday Cottages, Luxury Portland Holiday Cottages

5 Star Portland Holiday Cottages to suit all tastes and budgets. 5 star Portland holiday cottages sleeping five to twenty people. You can get results that match your exact needs by refining the results further using the options below. Click on the holiday cottage image or more details button to be taken to the cottages full information..

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Pennsylvania Castle

Pennsylvania Castle - Wakeham

  • 20

Prices from £7,200 per week

Pennsylvania Castle is a magnificent castle dating back to 1797 resting on a cliff top on Portland and set in stunning grounds with panoramic sea views. It is the perfect location for special occasions, reunions or family holidays. The castle can be hired out exclusively for a relaxing week or...

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Pennsylvania Castle, Cape Schanck

Pennsylvania Castle, Cape Schanck - Wakeham

  • 6

Prices from £2,592 per week

Pennsylvania Castle, Cape Schanck is your own fairytale getaway in 5 star gold luxury. This 200 year old castle, made from Portland Stone is now welcoming groups and families to enjoy the spectacular grounds, lavish rooms and amazing facilities for the first time. Down the gated, private driveway...

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Pennsylvania Castle, Print Hall

Pennsylvania Castle, Print Hall - Wakeham

  • 10

Prices from £4,320 per week

Pennsylvania Castle, Print Hall is your own fairytale getaway in 5 star gold luxury. This 200 year old castle, made from Portland Stone is now welcoming groups and families to enjoy the spectacular grounds, lavish rooms and amazing facilities for the first time. Down the gated, private driveway to...

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Pennsylvania Castle, Margaret River

Pennsylvania Castle, Margaret River - Wakeham

  • 8

Prices from £3,456 per week

Pennsylvania Castle, Margaret River is your own fairytale getaway in 5 star gold luxury. This 200 year old castle, made from Portland Stone is now welcoming groups and families to enjoy the spectacular grounds, lavish rooms and amazing facilities for the first time. Down the gated, private driveway...

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Pennsylvania Castle, Raffles

Pennsylvania Castle, Raffles - Wakeham

  • 14

Prices from £6,048 per week

Pennsylvania Castle, Raffles is your own fairytale getaway in 5 star gold luxury. This 200 year old castle, made from Portland Stone is now welcoming groups and families to enjoy the spectacular grounds, lavish rooms and amazing facilities for the first time. Down the gated, private driveway to the...

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Pennsylvania Castle, Half Moon

Pennsylvania Castle, Half Moon - Wakeham

  • 12

Prices from £5,184 per week

Pennsylvania Castle, Half Moon is your own fairytale getaway in 5 star gold luxury. This 200 year old castle, made from Portland Stone is now welcoming groups and families to enjoy the spectacular grounds, lavish rooms and amazing facilities for the first time. Down the gated, private driveway to...

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Shearwater

Shearwater - Wakeham

  • 6

Prices from £414 per week

Shearwater is a newly built three bedroom house, set over three floors, designed by an award-winning team and located on the east coast of Portland. It offers superb views of Pennsylvania Castle and out to the sea. The property is a highly energy efficient ‘Passivhaus’ eco-home,...

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Bayview Cottage

Bayview Cottage - Fortuneswell

  • 5

Prices from £665 per week

Bayview is in a spectacular location with a panoramic view of the whole of the local Jurassic Coast, overlooking Weymouth Bay, Portland Harbour, Chesil Beach and Lyme Bay.All the photos on both this page and on the gallery in the next tab are taken from the property. It has perhaps the most...

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The Old Portland Courthouse

The Old Portland Courthouse - Fortuneswell

  • 8

Prices from £1,126 per week

The Old Portland Courthouse is a grade II listed building dating back to c1904. It is in a wonderful position with panoramic sea views across Chesil Beach and Lyme Bay. The building has been sympathetically converted to a very high standard and many original features remain giving it a...

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Cove Lodge

Cove Lodge - Wakeham

  • 6

Prices from £472 per week

Set high on the cliff overlooking the sea with panoramic views over Freshwater Bay, Cove Lodge sits next to Cove Park and Pennsylvania Castle. With some of the best sea views on Portland you can sit back, relax and watch the world sail by. Owned by the same people that run Penn Castle, their...

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Seahaven

Seahaven - Chiswell

  • 6
  • N/A

Prices from £450 per week

Seahaven is a modern house with space, 3 bedrooms, partial sea views and within walking distance of Chesil Beach. Situated in Ben Ainslie Square, Seahaven has a private garden and barbecue, perfect for relaxing after a days exploring. Pubs, cafes, restauarants, the marina, National Sailing Academy...

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The Chalet

The Chalet - Fortuneswell

  • 5
  • N/A

Prices from £150 per week

”Portland Sailing Accommodation run by sailors for sailors and their families” but not just for sailors! This accommodation will suit anyone looking for self-catering accommodation on Portland throughout the year. Chalet accommodation in the grounds of Fortune House. Sleeps up to 5...

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