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Holiday Cottages in Portland

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Photo of Larkrise

Larkrise

Sleeps: 5 Rooms: 3 From €330 weekly
With a cosy open fire this cottage was once home to the famous Stone Carver Skylark Durston, whose work can be seen throughout. From the garden, wonderful coastal and sea views can be enjoyed, and Por...
From €330 weekly
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Photo of Limestone Cottage

Limestone Cottage

Sleeps: 6 Rooms: 3 From €393 weekly
Sea views from rear of cottageSet at the southern point of Portland with great coastline views. This charming terraced holiday cottage is an ideal touring base. Close by are footpaths leading to the S...
From €393 weekly
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Photo of Lime Cottage

Lime Cottage

Sleeps: 6 Rooms: 3 From €411 weekly
This 1850s cottage, one of a row, offers a great holiday location to enjoy the best of Dorset. Totally renovated by the owners, it presents a contemporary home from home. The cottage is set over three...
From €411 weekly
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Photo of Trevina

Trevina

Sleeps: 4 Rooms: 2 From €306 weekly
Situated in Weston in the heart of Portland, this semi-detached holiday home for four is ideally suited for exploring this scenic area, along with Weymouth and Dorchester with their many attractions....
From €306 weekly
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Photo of Leam House

Leam House

Sleeps: 8 Rooms: 4 From €835 weekly
Situated in the heart of Portland, this terraced house is an excellent holiday location to enjoy the best of west Dorset, from Swanage in the east, all the way to Lyme Regis, and taking in some breath...
From €835 weekly
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Photo of Canute Cottage

Canute Cottage

Sleeps: 5 Rooms: 2 From €503 weekly
This cosy, terraced holiday cottage is set in a quiet street, just a few hundred yards from the southern end of Chesil Beach. Portland harbour and castle, Portland Bill, Weymouth, with its beach and h...
From €503 weekly
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Photo of Freshwater Bay View

Freshwater Bay View

Sleeps: 2 Rooms: 1 From €315 weekly
Situated on the southern edge of Portland with views over Freshwater Bay, this semi-detached, single-storey holiday home lies ½ mile from Portland Bill Lighthouse. It is in a great location to explore...
From €315 weekly
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Photo of Sea Stones

Sea Stones

Sleeps: 6 Rooms: 4 From €383 weekly
Explore Chesil Beach and the Jurassic CoastThis characterful, Grade II listed terraced holiday cottage is set in the heart of Portland, under a mile from the beach at Church Ope Cove. It has easy acce...
From €383 weekly
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Photo of Pebbles

Pebbles

Sleeps: 6 Rooms: 3 From €359 weekly
Close to the seafront at Chiswell near the southern end of the famous Chesil Beach, this charming refurbished, 200 year old holiday cottage retains period features, offering stylish and comfortable ac...
From €359 weekly
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Photo of The Porthole

The Porthole

Sleeps: 4 Rooms: 2 From €386 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 €386 weekly
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Photo of The Olympus Penthouse

The Olympus Penthouse

Sleeps: 4 Rooms: 2 From €637 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 €637 weekly
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Photo of Stonecleave

Stonecleave

Sleeps: 10 Rooms: 5 From €744 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 €744 weekly
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Photo of Sea Pinks Cottage

Sea Pinks Cottage

Sleeps: 6 Rooms: 3 From €458 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 €458 weekly
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Photo of Pennsylvania Castle

Pennsylvania Castle

Sleeps: 20 Rooms: 9 From €14320 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 €14320 weekly
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Photo of Jurassica House

Jurassica House

Sleeps: 8 Rooms: 4 From €685 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 €685 weekly
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Photo of Chesil View House

Chesil View House

Sleeps: 6 Rooms: 3 From €458 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 €458 weekly
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Photo of Elizabethan House

Elizabethan House

Sleeps: 7 Rooms: 4 From €553 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 €553 weekly
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Photo of 83 Ocean Views

83 Ocean Views

Sleeps: 4 Rooms: 2 From €386 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 €386 weekly
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Photo of Cove Lodge

Cove Lodge

Sleeps: 6 Rooms: 3 From €685 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 €685 weekly
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Photo of 65 Ocean Views

65 Ocean Views

Sleeps: 4 Rooms: 2 From €422 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 €422 weekly
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Photo of 82 Ocean Views

82 Ocean Views

Sleeps: 4 Rooms: 2 From €386 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 €386 weekly
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Photo of 66 Ocean Views

66 Ocean Views

Sleeps: 6 Rooms: 2 From €386 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 €386 weekly
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Photo of 167 Ocean Views

167 Ocean Views

Sleeps: 4 Rooms: 1 From €338 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 €338 weekly
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Photo of 105 Ocean Views

105 Ocean Views

Sleeps: 4 Rooms: 2 From €494 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 €494 weekly
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Photo of The Old Portland Courthouse

The Old Portland Courthouse

Sleeps: 8 Rooms: 4 From €1006 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 €1006 weekly
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Photo of Jurassic Coast House

Jurassic Coast House

Sleeps: 8 Rooms: 4 From €878 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 €878 weekly
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Photo of Chesil View Apartment

Chesil View Apartment

Sleeps: 4 Rooms: 2 From €362 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 €362 weekly
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Photo of Osprey House

Osprey House

Sleeps: 7 Rooms: 4 From €596 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 €596 weekly
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Photo of The View

The View

Sleeps: 6 Rooms: 3 From €636 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 €636 weekly
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Photo of Admirals View

Admirals View

Sleeps: 8 Rooms: 4 From €792 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 €792 weekly
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Photo of The Tides

The Tides

Sleeps: 6 Rooms: 3 From €563 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 €563 weekly
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Photo of Sunset Lodge

Sunset Lodge

Sleeps: 6 Rooms: 3 From €517 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 €517 weekly
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Photo of Alpen Rose Cottage

Alpen Rose Cottage

Sleeps: 5 Rooms: 3 From €488 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 €488 weekly
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Photo of Neptune Cottage

Neptune Cottage

Sleeps: 5 Rooms: 3 From €463 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 €463 weekly
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Photo of Bowman's Cottage

Bowman's Cottage

Sleeps: 4 Rooms: 2 From €411 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 €411 weekly
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Photo of Olympic Cottage

Olympic Cottage

Sleeps: 4 Rooms: 2 From €488 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 €488 weekly
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