When only the best will do then choose a 5 star rated Portland holiday Cottage. All these cottages have either been rated 5 stars or 5 star gold by Visit England. With prices from as low as £150 you will be pleasantly surprised. We have luxury cottages sleeping between 4 to 20 and you can refine your search further by using the options below.
Click on the options below to show cottages that fit your exact needs.
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...More Details
”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...More Details
Fishermans cottage in Southwell village is a charming, detached 18th century cottage with excellent views across the sea. It has recently been renovated with full central heating throughout. On the ground floor is a large lounge/diner with sea views, a further reception room, a fully equipped...More Details
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,...More Details
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...More Details
Pebble Reef cottage is a traditional Quarryman's cottage full of character and lovingly renovated to bring it into the 21st century. The main living area downstairs is open plan. The lounge leads into the kitchen diner and through French doors leads you out to a bright and...More Details
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 unique...More Details
Spinnaker House is a delightful 3-bedroomed Victorian cottage. It is situated only 5 minutes' walk from Chesil Beach and less than a 1 mile walk to Weymouth and Portland National Sailing Academy (WPNSA). The facilities and location make it an ideal base for year round holidays on the...More Details
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...More Details
Seagull Cottage is specifically designed and equipped for the needs of sailors and their support teams. It is located just one mile from the Weymouth and Portland National Sailing Academy, the 2012 Olympic Sailing venue. The WPNSA is easily accessible on foot (15 mins), by cycle (5 mins), or by...More Details