Portland holiday cottages that sleep 8 or more guests including dog friendly cottages. With prices from as low as £494 per week Dorset is an affordable and beautiful destination. We have large cottages catering for up to 20 guests. You can further refine your requirements by using the options below.
Click on the options below to show cottages that fit your exact needs.
Leam House is a large, terraced cottage in Wakeham sleeping up to 8 and accepting 2 pets. Set over 3 floors all 4 bedrooms are en-suite. Leam House has an enclosed garden with a heated hot tub to relax in - perfect after exploring the many attractions and activities the area is known for. The...More Details
Pitt Hayes Cottage is set in a beautiful position with unrivalled views over Portland Harbour, Chesil Beach and the Jurassic Coast. Located in Fortuneswell, Portland, on clear days you can see all the way round to Lyme Regis. You will spend a lot of time in the garden losing yourself in the coastal...More Details
Jurassic Coast House is part of a development of sustainable eco-friendly homes that were built to house the athletes at the 2012 Olympics. Located in Fortuneswell, Portland and set over three floors with views to Chesil Beach and benefiting from a roof terrace. You are just a few minutes walk to...More Details
Ideal for small groups, couples and families with extensive sea views, 65 Fortuneswell sleeps up to 6 people comfortably in either single/twin or king-size beds. Situated in a central position on the lower part of the island, it is ideal for guests visiting the Weymouth and Portland National...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
Jurassica House is located in an architecturally modern new development, called Officers Field. The Developer has been voted Supreme Winner of the Housing Design Awards for the innovative eco-friendly development. The houses are part of our Olympic legacy, home to the athletes during the sailing...More Details
9 Sidon Mews is a fantastic holiday cottage with stylish interior and sunny garden. The property benefits from two living areas and has four bedrooms. You have sea views over Portland Harbour and the 18 miles of Chesil beach is just a short walk away. The National Sailing Academy is also a short...More Details
Quarries Reach is ideal for small groups, couples and families - fabulous rural and sea views. Sleeps up to 10, 8 ( 2). A new spacious detached house with a safe, secluded and walled garden. Situated in a prime position on top of the island with spectacular rural and sea views looking towards...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