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Holiday Cottages in Portland

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Photo of The Porthole

The Porthole

Sleeps: 4 Rooms: 2 From €383 weekly
Set in a prime position for exploring the picturesque island of Portland is The Porthole, a bright and modern third floor apartment with two spacious bedrooms. When you step inside, you’ll find...
From €383 weekly
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Photo of Stonecleave

Stonecleave

Sleeps: 10 Rooms: 5 From €737 weekly
Stonecleave is part of a very special group of properties owned by Pennsylvania Castle Estate (www.thepenn.co.uk) providing luxury accommodation on the island. A bright and inviting home where you&rsq...
From €737 weekly
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Photo of Sea Pinks Cottage

Sea Pinks Cottage

Sleeps: 6 Rooms: 3 From €454 weekly
Sea Pinks Cottage was built around 1860 and is a fine example of a traditional fisherman’s cottage built with Portland stone. The property has been refurbished to a high standard with the bedro...
From €454 weekly
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Photo of Pennsylvania Castle

Pennsylvania Castle

Sleeps: 20 Rooms: 9 From €14188 weekly
Pennsylvania Castle is an incredible example of English history, a luxuriously modernised home wrapped in over 200 years of Portland stone and stories! For most of its life the castle has just hosted...
From €14188 weekly
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Photo of The Olympus Penthouse

The Olympus Penthouse

Sleeps: 4 Rooms: 2 From €642 weekly
Ocean Views is perched in an enviable position on Portland’s seafront, situated on the Jurassic coast beside Chesil Beach. The Olympus Penthouse is a two bedroom, fifth floor apartment with grea...
From €642 weekly
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Photo of Jurassica House

Jurassica House

Sleeps: 8 Rooms: 4 From €678 weekly
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 climbing, bir...
From €678 weekly
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Photo of Elizabethan House

Elizabethan House

Sleeps: 7 Rooms: 4 From €548 weekly
Elizabethan House is 17th Century Grade II listed property located in Portland, situated just 500 yards from Chesil Beach and within a short walk from the National Sailing Academy. Internally, the pro...
From €548 weekly
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Photo of Cove Lodge

Cove Lodge

Sleeps: 6 Rooms: 3 From €678 weekly
Cove Lodge grants its guests the opportunity to delight themselves with what Portland is famous for - the most amazing sea views. The property owns three large bedrooms (one with en suite) and can com...
From €678 weekly
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Photo of Chesil View House

Chesil View House

Sleeps: 6 Rooms: 3 From €454 weekly
Chesil View House offers stylish accommodation that was originally a fisherman’s cottage in the beautiful village of Fortuneswell, nestled amongst the hills of Portland. Internally the property...
From €454 weekly
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Photo of 83 Ocean Views

83 Ocean Views

Sleeps: 4 Rooms: 2 From €383 weekly
Ocean Views perched in an enviable position on Portland’s seafront, situated on the Jurassic coast beside Chesil Beach. The apartments have been finished to a high standard with high quality flo...
From €383 weekly
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Photo of 82 Ocean Views

82 Ocean Views

Sleeps: 4 Rooms: 2 From €398 weekly
82 Ocean Views is a stylishly furnished apartment with partial sea views, located on the fourth floor of the development, in an enviable position on Portland's seafront. The apartment has been fin...
From €398 weekly
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Photo of 65 Ocean Views

65 Ocean Views

Sleeps: 4 Rooms: 2 From €418 weekly
Ocean Views perched in an enviable position on Portland’s seafront, situated on the Jurassic coast beside Chesil Beach. The development also features a health and fitness centre complete with an...
From €418 weekly
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Photo of 167 Ocean Views

167 Ocean Views

Sleeps: 4 Rooms: 1 From €340 weekly
Ocean Views is situated on the Jurassic coast beside Chesil Beach. The development also features a health and fitness centre complete with an indoor swimming pool. Being home to some of the finest sma...
From €340 weekly
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Photo of 105 Ocean Views

105 Ocean Views

Sleeps: 4 Rooms: 2 From €489 weekly
Situated on Portland’s scenic seafront with the famous Chesil Beach almost on your doorstep is 105 Ocean Views, a contemporary and stylish two bedroom apartment. With sophisticated furnishings a...
From €489 weekly
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Photo of Langham Cottage

Langham Cottage

Sleeps: 4 Rooms: 2 From €435 weekly
New for January 2017. Situated on the Isle of Portland, just a few moments from the acclaimed Chesil Beach, Langham Cottage is a traditional style terraced house with magnificent views out to sea. Rec...
From €435 weekly
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Photo of The Old Portland Courthouse

The Old Portland Courthouse

Sleeps: 8 Rooms: 4 From €1026 weekly
The Old Portland Courthouse overlooks a wonderful expanse of Chesil Beach out to Lyme Bay and is within easy walking distance of the Weymouth and Portland Sailing Academy where sailing events for the...
From €1026 weekly
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Photo of Admirals View

Admirals View

Sleeps: 8 Rooms: 4 From €808 weekly
Admiral's View is a unique luxurious penthouse conversion in Dorset beside the Jurassic coastline in Portland. The roof terrace enjoys wonderful views of Portland Harbour, Weymouth Bay and Lyme Bay in...
From €808 weekly
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Photo of The View

The View

Sleeps: 6 Rooms: 3 From €649 weekly
The View is located in an elevated position just a short strollfrom Chesil beach and promenade, which is part of the coastal path around Portland. Chesil beach stretches along the Jurassic Coast, wher...
From €649 weekly
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Photo of Chesil Cove Cottage

Chesil Cove Cottage

Sleeps: 6 Rooms: 3 From €528 weekly
Inside this traditional fisherman's cottage, you will find a contemporary interior with comfortable lounge and two bath/shower rooms. There is a kitchen and dining area offering a pleasant communal ar...
From €528 weekly
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Photo of The Tides

The Tides

Sleeps: 6 Rooms: 3 From €608 weekly
Situated on the World Heritage Coast in Dorset, at The Tides you can enjoy living like an Olympian! The Tides was built to house a Sailing team during the 2012 Olympics. Situated on The Officer's Fiel...
From €608 weekly
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Photo of Neptune Cottage

Neptune Cottage

Sleeps: 5 Rooms: 3 From €472 weekly
Situated behind the sea wall and just a minute or so from the beach, Neptune Cottage is a delightful terraced fisherman's cottage dating back 200 years but now fully refurbished and updated. Located i...
From €472 weekly
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Photo of Osprey House

Osprey House

Sleeps: 7 Rooms: 4 From €608 weekly
Osprey House Portland is located on the edge of the Isle of Portland on the World Heritage Coast in Dorset. Situated on The Officer's Field, a stunning residential development, it originally housed an...
From €608 weekly
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Photo of Bowman's Cottage

Bowman's Cottage

Sleeps: 4 Rooms: 2 From €419 weekly
Situated on the rugged and beautiful isle of Portland, Bowman's is a character, terraced Dorset holiday cottage located on the wide avenue which is Wakeham. Internally, the owners have sympathetically...
From €419 weekly
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Photo of Olympic Cottage

Olympic Cottage

Sleeps: 4 Rooms: 2 From €497 weekly
Olympic Cottage is situated on The Officer's Field, a stunning residential development built originally to house athletes during the 2012 Olympic sailing events. The property is located on the edge of...
From €497 weekly
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Photo of Chesil View Apartment

Chesil View Apartment

Sleeps: 4 Rooms: 2 From €370 weekly
Chesil View Apartment is a high specification two bedroom second and third floor apartment with unrivalled panoramic sea views of Chesil beach stretching from Portland to Lyme Regis. Inside there is a...
From €370 weekly
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Photo of Jurassic Coast House

Jurassic Coast House

Sleeps: 8 Rooms: 4 From €896 weekly
Jurassic Coast House is situated on The Officer's Field, a stunning residential development built originally to house athletes during the 2012 Olympic sailing events. The property is located on the ed...
From €896 weekly
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Photo of Sunset Lodge

Sunset Lodge

Sleeps: 6 Rooms: 3 From €528 weekly
Sunset Lodge is located approximately 10 yards from Chesil beach and promenade, which is part of the coastal path around Portland. Chesil beach is part of the Jurassic Coast, where you can enjoy gener...
From €528 weekly
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Photo of Alpen Rose Cottage

Alpen Rose Cottage

Sleeps: 5 Rooms: 3 From €497 weekly
Alpen Rose Cottage is a restored traditional fisherman's cottage. Inside this large and spacious property the rooms have been furnished to a high standard. Easton Square is only a short walk away with...
From €497 weekly
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