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

Cottage | 2 bedrooms | Sleeps 5

Situated in a quiet location at the southern end of the island with stunning sea views just a stone's throw away from beautiful coastal walks and scenery - near Portland Bill lighthouse and the Lobster Pot restaurant.

House | 2 bedrooms | Sleeps 6

Cliffwalk Cottage is a newly built, two bedroom house, which can sleep up to 6 people.

Apartment | 2 bedrooms | Sleeps 3

A two bedroom holiday apartment, close to Portland Harbour, Portland Castle and the National Sailing Academy.

Cottage | 3 bedrooms | Sleeps 6

4 Sea View 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 a fabulous kitchen and comfortable accommodation.

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.

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.

Cottage | 3 bedrooms | Sleeps 6

Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Ideal for Sailing academy, bird watching or just a quiet getaway. The ideal location for the 2012 Olympic Sailing whether supporting, taking part or just for the atmosphere.

Cottage | 3 bedrooms | Sleeps 5

A charming cottage in this pretty road, a short walk down to Chesil Beach and Cove and easy going of the National Sailing Academy at Portland Harbour. Relaxing, walking, sailing - some of the options in easy reach of this holiday cottage.

Apartment | 1 bedroom | Sleeps 2

Very spacious self catering “studio style” apartment close to Portland Bill & Jurassic coastal scenery. Sleeps 2+ cot. Flexible living area. Large enclosed sun-trap patio with safe parking. Very well equipped with 32” Flat screen Sat. TV & WiFi Broadband. Pets welcome. Ideal for young/mature couples. Seating for four plus. Car unnecessary, close to walks/sailing/sports.

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.

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.

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

3 bedroom stone cottage - with a 4 star VE rating - modernised to a high standard, in a village location near all amenities and the sea. Ideal for couples or families either wishing to relax, take part in local sports or water sports, or explore the island and Weymouth. A character-full Victorian cottage on a quirky island with garden and parking: a warm welcome awaits you!

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.

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.

Cottage | 3 bedrooms | Sleeps 6

Pebble Reef is a traditional Quarryman’s Cottage, full of character but lovingly renovated to include all the modern comforts you need.

Studio | Sleeps 2

Open all year. Tranquil, warm retreat above Church Ope Cove. Self catering Studio for 2 set on the cliff path a 7 minute walk from the nearest village and major amenities. 5 minute drive from Olympic Sailing Academy. Wet room, Wifi, Woodburner, Ipod dock. Pets welcome. Suits romance and retreat, sail, walk, climb, work or study with Wifi, Pets and walkers Welcome Awards.

House | 3 bedrooms | Sleeps 6

Within sound of the breaking surf, take breakfast on the balcony and enjoy stunning views of Chesil Beach. Situated in a quiet area of Fortuneswell yet only a short walk from Shops, Restaurants, Pubs and Beach and 5 minutes from the Olympic Sailing Venue.

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

Very spacious self catering detached house close to Portland Bill and Jurassic coastal scenery. Sleeps up to 8 + cot in 4 bedrooms. Large enclosed family-friendly garden with safe parking. Very well equipped with 42” Flat screen Sat. TV and WiFi Broadband. Pets welcome. Ideal for families/large groups. Large, safe, grass garden. Car unnecessary, close to walks/sailing/sports.

House | 2 bedrooms | Sleeps 6

Hillside is a stunning fully refurbished Victorian house with views from a southwest facing garden overlooking Portland Harbour and WPNSA.Only five minutes walk from Chesil beach, Hillside was refurbished to be our home which we have chosen to allow others to enjoy. What other property on Portland has chandeliers ,roll top bath and feature wallpaper?

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.

House | 3 bedrooms | Sleeps 8

Contemporary Cottages are ideally situated for anyone visiting Weymouth and Portland in Dorset. Short breaks and weekly bookings are accepted throughout the year. You can book from any day of the week. Late arrivals and early check-outs are welcomed. Situated very near to the Weymouth and Portland National Sailing Academy.

Cottage | 2 bedrooms | Sleeps 4

A charming house in the middle of Fortuneswell, Portland. Centrally located, walking distance from Chesil Beach and Portland Harbour. Perfect for fishing, sailing, watersports and exploring Dorset. Weymouth and Portland offer a wealth of local historical sites of interest, events and attractions.

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.

House | 4 bedrooms | Sleeps 8

Beautifully renovated family house situated down a quiet lane, minutes from a picturesque cove and lovely cliff top walks.

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.

House | 4 bedrooms | Sleeps 10

The Gift House is a beautiful fully renovated and refurbished 4 bedroom house situated 2 minutes walk from the beach, with stunning panoramic sea views from all reception rooms and bedrooms stretching across Chesil Beach to the Olympic Sailing Village. The property is suited to outdoors enthusiasts and families. A perfect retreat with modern luxuries.

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 | 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.