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 bistro table and chairs. A perfect holiday location all year round, for either sun and relaxation, or enjoy activities like windsurfing, sailing, diving, rock climbing, fishing, walking and bird watching.

Pilgrims Cottage-Luxury Grade 1 Listed cottage

Take it easy at this unique and tranquil getaway. Come and unwind in our Grade 1 listed cottage set in the most beautiful street in gorgeous Cerne Abbas. Steeped in history you won’t want to leave this hidden gem. Out the front door are walks for miles and a visit to the Giant is a must! Then either cook up a storm in the well equipped kitchen , enjoy the garden with Big Green Egg bbq or wander down to the choice of three local pubs. The Sea is just a short 30 mins drive. Parking free opposite

Authentic, cosy, thatched cottage, mins from coast

Cosy Carters Cottage nestles in the peaceful Dorset hamlet of North Chideock, adjacent to 16th century Home Farm Cottage. A fab rambler's location, with EV charger, 40 mins walk from the Jurassic coastline, 3 thatched pubs, Spar shop, Felicity's Farm Shop, Hell's Lane smugglers hollow-way, Colmers Hill & Symondsbury Estate Cafe. 15 mins drive to Lyme Regis. The cottage is simply furnished - 2 bedrooms, (second at top of stairs) WC, kitchen & lounge. Guest parking with private, walled garden.

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.

Beautiful 2 bedroom cottage in glorious Dorset

Nestled in the picturesque Dorset countryside, this charming Portland stone cottage offers a quintessential English retreat. Set within the grounds of a historic Old Rectory, the property is surrounded by rolling hills, lush meadows, and the tranquil River Frome, providing an idyllic spot for a holiday. It is all on one level,we are able to rent out the whole cottage also which creates an additional 2 bedrooms for extended family - we rarely rent this out to another party and is mostly empty.

Romantic hillside hideaway with outstanding views

A unique and romantic hideaway, Quarryman's Cottage is dinner on the roof terrace watching the sunset over Lyme Bay & Charmouth, stargazing from the luxury freestanding bath, epic views from the double shower, reading under the old oak tree, BBQ's & firepits, leisurely walks to The Anchor at Seatown via Golden Cap or the coastal path, the sound of birdsong, the glimpse of a deer, curling up in front of the wood burner in winter. It is a tranquil & heavenly escape from the bustle of daily life.

Cottage Near Beach and 3 Pubs. South facing garden

Enjoy coastal walks straight from the door whilst staying in this stylish, cosy cottage. Lovely hill views from the garden with decked area and 3 excellent pubs all walkable from the cottage and just a 20 minute walk to the beach at Seatown. Buses every hour so you can walk one way and ride back. Spar shop with EV charging just down the road. Greenwich Cottage in Chideock is perfect for a restful break with all the mod-cons you expect with good wifi and smart TV. Cosy log-burner. Parking.

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.

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

Cobb Cottage - Harbourside, permit parking

Cobb Cottage is a stylish hideaway, tucked down a cobbled side street in the heart of Weymouth's historic harbour. The cottage has been lovingly converted from a former bookshop into a contemporary, centrally located holiday home with easy access to Weymouth harbour. Perfectly suited for two couples or a family, with three bedrooms and two bathrooms. There is a parking permit to for one car which provides free parking on street outside the cottage, or in a nearby car park. Dog friendly!

Cove Garden Cottage with enclosed sea view garden

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.

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.