Holiday rentals in Portland, UK England - Holiday homes to rent - Book direct

Cottage | 3 bedrooms | Sleeps 7

Character cottage over three floors, sleeps seven comfortably. A short walk from Chesil Beach and the local amenities, the National Sailing Academy and Portland Harbour. The harbour is found within a short drive or leisurely walk from the property. At the centre of the Jurassic Coast, Portland is an ideal base for water sports, walking & exploring Dorset.

Apartment | 1 bedroom | Sleeps 3

The Library Apartment is a cosy apartment with wonderful views over Chesil Beach; ideal for watching the sun go down. Weymouth & Portland is an excellent base for exploring South Dorset’s coast and countryside.

Cottage | 2 bedrooms | Sleeps 4

Built in the 1800's, this sweet little original Portland stone Fisherman's cottage promises a lovely holiday experience. Artist Cottage sleeps four people in two bedrooms and has been delightfully restored.

House | 4 bedrooms | Sleeps 7

Sea Dragon is a charming four-bedroom property on Portland very close to Chesil Beach. The house is very well equipped and a short walk from the local amenities, including pubs and restaurants. The National Sailing Academy can be reached in a few minutes by car. Weymouth & Portland is an excellent base for exploring South Dorset’s coast and countryside.

Apartment | 2 bedrooms | Sleeps 4

Frigate Apartment is a stunning holiday apartment with sea views situated in the eye-catching Ocean Views development, close to Portland Harbour and the National Sailing Academy. The development boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool.

Cottage | 3 bedrooms | Sleeps 6

Tompot Cottage is a charming, cosy, Grade II listed, Portland stone holiday home in Chiswell, a stone's throw across the road from Chesil Beach. It dates from around 1650, and has a wealth of original features. A pebble's throw from Chesil Beach and a level walk to Portland Harbour.

House | 4 bedrooms | Sleeps 10

Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. This deceptive very comfortable house offers home from home facilities with everything to entertain a family.

Cottage | 4 bedrooms | Sleeps 8

Mallams Cottage is a beautifully finished period cottage, well located for Chesil Beach, Portland Harbour and the National Sailing Academy. Close to the best sailing waters in Europe.

House | 2 bedrooms | Sleeps 5

Stunning location with probably the best views on Portland, overlooking Weymouth Bay, Portland Harbour and Chesil Beach. Attractive 2 bedroom house with gardens, surrounded by open hillside with uninterupted views of the sun setting over Lyme Bay. Breath-taking panoramic views. Ideal situation for exploring Portland's natural heritage.

Cottage | 2 bedrooms | Sleeps 4

White Sails offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering spacious and comfortable accommodation a short walk from Chesil Beach.

House | 4 bedrooms | Sleeps 8

This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere.

Cottage | 3 bedrooms | Sleeps 5

A character terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only a few minutes walk from the famous Chesil Beach, 5 minutes drive from the National Sailing Academy and easy walk ing distance to the Olympic Sailing Village. Excellent restaurants and pubs within walking distance of the cottage. Free Wi-Fi.

House | 4 bedrooms | Sleeps 10

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 Dorset's Jurassic Coast.