Holiday houses in Isle of Portland

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Top-rated holiday rentals in Isle of Portland

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Superhost

Cottage in Dorset

4.88 out of 5 average rating, 355 reviews

18th Century Coastal Cottage

This historic home features original stone floors, rustic wood beam ceilings, a wood-burning fireplace, modern finishes, a sauna, and a private back patio overlooking the beach. Breathe in the refreshing ocean air from this hillside retreat. I’m sorry I have a no pets policy at the cottage. This cottage has steep stairs, low ceilings, a very low rise bed and a low sofa as seen in the pictures. 60 Mallams was built in approximately 1760 and still has many rustic features throughout. The cottage has two levels, ground floor consists of open plan lounge leading to the kitchen then conservatory with shower room. Which opens out into courtyard garden with a terrace and sea views. 1st floor has the main bedroom with a super king size bed and separate bathroom with a free standing bath with room for two.. Private parking on driveway 24hr key access safe by the front door I can be contacted at any time throughout your stay. The property is located just a five minute walk from Chesil Beach. It is also close to a number of the town's local shops and cosy pubs. There’s plenty of coastal walks all around Portland The sailing club is close offering various water sports There is bus services to and from Weymouth. There are amazing coastal walks around Portland. Please be mindful of the rubbish I have food waste bins , glass only tubs and the larger of the wheelie bins (green) are recycling only ( cans paper and plastic) and the black bins are general rubbish.. please be careful with the rubbish because if it's all mixed up the bin men won't take it away...

Guest favourite

Townhouse in Dorset

4.95 out of 5 average rating, 203 reviews

CLOUD 9 🦚 Homely & Happy 😊 Near the Beach 🌊🐟🌞

Welcome home. Welcome to CLOUD9🫶🏽 Renovated and designed with love by our family🧡 Boutique vintage-modern velvet luxury in the heart of Fortuneswell on the South-west Isle of Portland🌊 Living/dining room, kitchen, downstairs w/c, enclosed garden. Spacious shower room plus 3 themed bedrooms 🦚🌸 with sea views⛵️ Chesil beach, co-op local, fish & chips & friendly pubs all close-by🐟 😊 Super fast 100mb+ WiFi. Fully equipped kitchen. *If booking for 1-2 only, loft room will be locked shut.

Guest favourite

Cottage in Easton

4.93 out of 5 average rating, 205 reviews

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.

Guest favourite

Condo in Dorset

4.91 out of 5 average rating, 483 reviews

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

Top Guest favourite

Bungalow in Dorset

4.95 out of 5 average rating, 177 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this your own space within owner occupied property. Explore Portland, an Island that features breathtaking views, beautiful walks. Castles, 3 lighthouses. Chesil beach. a Museum, rock climbing, wildlife, water sports. History of smugglers & pirates explore Church Ope Cove. 20 min on bus to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem. Not suitable for infants (Adults only)

Guest favourite

Cottage in Easton

4.92 out of 5 average rating, 224 reviews

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.

Top Guest favourite

Guesthouse in Easton

4.97 out of 5 average rating, 112 reviews

Characterful 2-bedroom cozy cottage with garden

Enjoy a stylish experience at this cozy, centrally-located cozy two-bedroom cottage with modern facilities plus Sky, coffee machine and private garden. Bedroom one has a double bed, bedroom two is a twin with two single beds. Walking distance from shops, cafes, Church Ope beach, cliff paths. Visit Portland to sail, dive, rock climb, bike ride, hike, visit art exhibitions, relax and explore. Unsafe for pre-school kids. Sorry no under 4 years old . No smoking 🚭

Top Guest favourite

Cottage in Fortuneswell

4.99 out of 5 average rating, 281 reviews

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.

Guest favourite

Holiday home in Easton

4.94 out of 5 average rating, 179 reviews

Quirky 2 bed holiday home with hot tub and sauna.

Newly built 2 bedroom cottage with hot tub and sauna located in Easton on Portland in Dorset. This unique home is built in Portland stone and has a ground floor outdoor space with patio and outdoor oven area as well as having an upstairs outdoor mezzanine area with bi-folding doors. The main living space that includes a 90” television. All equipped with sky Q including sports. Both bedrooms have super king beds and are en-suite with showers and jacuzzi baths.

Superhost

Tiny home in Dorset

4.85 out of 5 average rating, 251 reviews

Studio Pod 2

Pod 2 has a modern, fully equipped kitchen, bathroom, sofa, TV and drop-down double sofa bed. You can sit in bed with a view of the sea or chill on the deck with a glass of wine on a sunny evening. Our Pods come with bed linen and towels included. -Fantastic elevated sea views from the top level of Park (The view is shown in the images) -Large decking with outside seating -Innovative pull-down double bed and fold away sofa -No pets

Guest favourite

Condo in Portland

4.95 out of 5 average rating, 109 reviews

Couples Luxury Retreat

Beautiful views, central location and ample free parking. Ideal for a couples getaway. Well equipped kitchen, luxury bedding and a sleek shower room. The Devonshire apartment is a spacious holiday apartment on Portland, in the heart of the Jurassic coastline. Just a few moments walk from the quaint Easton square with local businesses including shops, pubs, takeaways and cafes.

Guest favourite

Guest suite in Dorset

4.85 out of 5 average rating, 191 reviews

The Backhouse, Southwell, Portland

A characterful, rustic old stable which has been converted into a small self contained holiday let. The accommodation is comfortable and full of character and quirks. The property is 3 minutes walk from the Jurassic coast path and provides easy access for Climbers, Walkers, Birdwatchers and Watersports. we do have dogs living in our home who do have access to the garden