Cottage holiday rentals in Isle of Portland

1888 Portland stone cottage

1888 Portland stone cottage, with many original features. Stone fireplace with log burner. Cosy 2 bedroom, 3 storey cottage located within easy walking distance of Easton Square, which has local amenities, including grocery stores, chemist, pubs and cafes. Small sunny aspect courtyard with bbq, bistro table and chairs A perfect holiday location all year round, for either sun and relaxation, or activities windsurfing, sailing, diving, rock climbing, fishing or just walking and bird watching.

Chesil Cove Holiday Cottage

A Grade II listed traditional characterful fisherman's cottage located adjacent to the iconic Chesil Cove on the isle of Portland, part of the Jurassic Coast. The cottage is small & cosy with two bedrooms, upstairs wetroom & modernised kitchen with solid wood breakfast bar. The wooden stairs are very steep & narrow so the property is not suitable for young children/those with mobility issues. An enclosed south-facing backyard is a suntrap for private sunbathing, drying swimming/diving gear etc.

Little Barn is a cosy dwelling in a remote valley

Little Barn is located in a remote valley between Upwey and Portesham near Weymouth in Dorset A converted Barn with a modern open plan interior. An adequate garden with Outdoor furniture and BBQ with an external secure store for bicycles etc. The area is good for walking (dogs welcome), many footpaths line the surrounding countryside. Hardy's monument is situated a few miles away. The area offers good cycling both on and off road. Good access to the Dorset coastline which is a short drive away.

Number 107, Isle of Portland, Dorset

Number '107' positioned on the Isle of Portland with its close proximity to Chesil Beach is a spacious, comfy & well equipped cottage within 5 mins walk of the beach. Situated close to all local amenities with shops, cafes & pubs all within a short walking distance. The cottage is perfect for families & couples looking for a cosy seaside retreat & those looking for a place to relax after a day of walking, climbing, and water sports. An ideal base for exploring Jurassic Coast and beyond.

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

Cove Garden Grade II Cottage

Magical sunsets and magnificent coastal walks. Stop the clock relax and enjoy all that this little haven on the Jurassic coast has to offer. Something for everyone from chilling and reading to water sports such as sailing, kite surfing and paddle boarding. There are plenty of local pubs, restaurants and cafes to choose from too. Some of the best in walking distance. The local art and music scene is very established. This is a great spot to explore the Dorset coast and venture inland.

Character cottage with sea views and parking

200-year old 'Quarryman's Cottage' is just a short walk from Chesil Beach and the South West Coast Path and the perfect base for a family holiday in Dorset. It offers a private balcony with stunning sea views, off-road parking, three bedrooms, and open plan dining/living room with log burner. The local area is fantastic for windsurfing, sailing, kitesurfing, paddleboarding, climbing, walking, bird-watching, diving and fishing. We hope you enjoy it as much as we do!

Maidenwell Cottage. Near Chesil Beach, Portland

Maidenwell Cottage is a Grade II listed period property on Portland, the southernmost point of the Jurassic Coast that has been refurbished to a high standard and designed to make you feel at home. Chesil Beach, local shops, cafes and pubs are all a within a short walking distance. Maidenwell Cottage is perfect for families and couples looking for a cosy seaside retreat and those looking for a place to relax following a day of walking, climbing and water sports.

Crows Nest - cosy, tiny cottage - all mod cons.

A charming cottage in Fortuneswell. Close to the National Sailing Academy and Chesil Beach. Living room/ bedroom, bathroom and separate kitchen and dinning area. Beautifully fitted in small proportions except the TV and shower. Small courtyard, keep bikes and equipment secure, outside drying area and Dri Buddie inside. Ideal base for two, sailing, diving, climbing and walking or just to mooch around enjoying the Jurassic coast.