menu

Holiday Cottages in Portland

Select a location
Photo of Brightstone Park

Brightstone Park

Sleeps: 4 Rooms: 2
Caravan with one master king size double with ensuite WC and one twin. Some with sea views. No pets.. Set in the grounds of a former royal castle, Cove Holiday Park enjoys an enviable cliff top settin...
Request to book
Photo of Brightstone Seaview

Brightstone Seaview

Sleeps: 4 Rooms: 2
Caravan with one master king size double with ensuite WC and one twin. Sea views. No pets.. Set in the grounds of a former royal castle, Cove Holiday Park enjoys an enviable cliff top setting on the u...
Request to book
Photo of Brightstone WF

Brightstone WF

Sleeps: 4 Rooms: 2
Caravan with one master double (twin by arrangement) with ensuite WC and one twin. Wet room. Wider door frames and sliding internal access doors. Elevated sea views. No pets. Suitable for parties incl...
Request to book
Photo of Brightstone

Brightstone

Sleeps: 4 Rooms: 2
Caravan with one master king size double with ensuite WC and one twin. Partial sea views.. Set in the grounds of a former royal castle, Cove Holiday Park enjoys an enviable cliff top setting on the un...
Request to book
Photo of The Olympus Penthouse

The Olympus Penthouse

Sleeps: 4 Rooms: 2 From €663 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 €663 weekly
Request to book
Photo of The Porthole

The Porthole

Sleeps: 4 Rooms: 2 From €374 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 €374 weekly
Request to book
Photo of Stonecleave

Stonecleave

Sleeps: 10 Rooms: 5 From €721 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 €721 weekly
Request to book
Photo of Sea Pinks Cottage

Sea Pinks Cottage

Sleeps: 6 Rooms: 3 From €443 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 €443 weekly
Request to book
Photo of Pennsylvania Castle

Pennsylvania Castle

Sleeps: 20 Rooms: 9 From €13868 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 €13868 weekly
Request to book
Photo of Jurassica House

Jurassica House

Sleeps: 8 Rooms: 4 From €663 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 €663 weekly
Request to book
Photo of 65 Ocean Views

65 Ocean Views

Sleeps: 4 Rooms: 2 From €409 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 €409 weekly
Request to book
Photo of Elizabethan House

Elizabethan House

Sleeps: 7 Rooms: 4 From €536 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 €536 weekly
Request to book
Photo of Cove Lodge

Cove Lodge

Sleeps: 6 Rooms: 3 From €663 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 €663 weekly
Request to book
Photo of 83 Ocean Views

83 Ocean Views

Sleeps: 4 Rooms: 2 From €374 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 €374 weekly
Request to book
Photo of Chesil View House

Chesil View House

Sleeps: 6 Rooms: 3 From €443 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 €443 weekly
Request to book
Photo of 82 Ocean Views

82 Ocean Views

Sleeps: 4 Rooms: 2 From €374 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 €374 weekly
Request to book
Photo of 167 Ocean Views

167 Ocean Views

Sleeps: 4 Rooms: 1 From €328 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 €328 weekly
Request to book
Photo of 105 Ocean Views

105 Ocean Views

Sleeps: 4 Rooms: 2 From €478 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 €478 weekly
Request to book
Photo of The Tides

The Tides

Sleeps: 6 Rooms: 3 From €561 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 €561 weekly
Request to book
Photo of Langham Cottage

Langham Cottage

Sleeps: 4 Rooms: 2 From €425 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 €425 weekly
Request to book
Photo of Chesil View Apartment

Chesil View Apartment

Sleeps: 4 Rooms: 2 From €361 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 €361 weekly
Request to book
Photo of St Johns View

St Johns View

Sleeps: 4 Rooms: 2 From €444 weekly
Located on the rugged and wild Dorset Coastal Isle of Portland, which forms part of the Jurassic Coast, the world heritage site, St. John's view is a modern detached house with sea views. Just around...
From €444 weekly
Request to book
Photo of The Old Portland Courthouse

The Old Portland Courthouse

Sleeps: 8 Rooms: 4 From €1003 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 €1003 weekly
Request to book
Photo of Admirals View

Admirals View

Sleeps: 8 Rooms: 4 From €790 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 €790 weekly
Request to book
Photo of The View

The View

Sleeps: 6 Rooms: 3 From €634 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 €634 weekly
Request to book
Photo of Chesil Cove Cottage

Chesil Cove Cottage

Sleeps: 6 Rooms: 3 From €516 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 €516 weekly
Request to book
Photo of Neptune Cottage

Neptune Cottage

Sleeps: 5 Rooms: 3 From €462 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 €462 weekly
Request to book
Photo of Osprey House

Osprey House

Sleeps: 7 Rooms: 4 From €595 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 €595 weekly
Request to book
Photo of Bowman's Cottage

Bowman's Cottage

Sleeps: 4 Rooms: 2 From €410 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 €410 weekly
Request to book
Photo of Olympic Cottage

Olympic Cottage

Sleeps: 4 Rooms: 2 From €486 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 €486 weekly
Request to book
Photo of Jurassic Coast House

Jurassic Coast House

Sleeps: 8 Rooms: 4 From €876 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 €876 weekly
Request to book
Photo of Sunset Lodge

Sunset Lodge

Sleeps: 6 Rooms: 3 From €516 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 €516 weekly
Request to book
Photo of Alpen Rose Cottage

Alpen Rose Cottage

Sleeps: 5 Rooms: 3 From €486 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 €486 weekly
Request to book
Holiday rental locations
Listing 1-33 of 33 Top Holiday Rentals
Results per page:
  • 10
  • 20
  • 50
With cookies we can give you the best experience on selfcatering.travel. By using our website, you consent to the use of cookies.