Holiday rentals in Isle of Portland

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Top-rated holiday rentals in Isle of Portland

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Cottage in Dorset

4.87 out of 5 average rating, 343 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...

Top guest favourite

Cottage in Easton

4.93 out of 5 average rating, 193 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

Apartment in Dorset

4.91 out of 5 average rating, 459 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

Guest favourite

Cottage in Easton

4.92 out of 5 average rating, 213 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

Tiny home in Portland

4.95 out of 5 average rating, 249 reviews

Coast - White Stones Studios

Come and enjoy our new and unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

Guest favourite

Tiny home in Dorset

4.86 out of 5 average rating, 339 reviews

The Zen Den🙏Relaxing🦋 Cosy🌸Idyllic🌊Location🌿

The Zen Den is an annexe off our bungalow, with own front door access. Bath with shower. Washing machine, microwave, fridge/freezer. No oven or hob, kitchenette for food prep, sofa bed & bistro set. Bedroom - Double bed with bamboo mattress topper for comfort, with garden view. Patio with seating area, beautiful garden with unbelievable sea views over the amazing Chesil Beach Jurassic Coastline🌊🌞 Back gate onto the Jurassic coastal path. Special Location 🌞 🌊🏝❤️ 🫂 😊

Guest favourite

Holiday home in Easton

4.94 out of 5 average rating, 162 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.

Top guest favourite

Guest house in Easton

4.97 out of 5 average rating, 104 reviews

Characterful 2-bedroom cozy cottage with garden

Enjoy a stylish experience at this 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 5 years old. No smoking 🚭

Guest favourite

Home in Dorset

4.87 out of 5 average rating, 119 reviews

Fair Winds House

Fair Winds offers a getaway just a stone's throw from the ocean and Portland Marina with allocated parking and enclosed garden. Wake up to sea views 2 minutes walk from Portland Castle Beach, or 5 minutes to the renowned Chesil Beach. We have a brilliant bakery and the beachside sauna, both just around the corner. For a peaceful retreat or an adventure by the sea, Fair Winds is an ideal base for exploring the wonders of Dorset's stunning coastline.

Guest favourite

Guest suite in Dorset

4.84 out of 5 average rating, 182 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

Guest favourite

Cottage in Dorset

4.86 out of 5 average rating, 412 reviews

Character cottage close to beach

Spacious and beautiful house 5 min walk to Chesil Beach. Free superfast wi-fi, well equipped kitchen including dishwasher and a cosy log burner in living room. Scandi style décor. Netflix and smart TV. Right in heart of Fortuneswell, Portland with some shops, pubs and restaurants close by. 10-15 min drive from Weymouth. Great for couples.

Top guest favourite

Bungalow in Dorset

4.94 out of 5 average rating, 125 reviews

Islands Wrest (The Cavern). Twin/Dbl Rm. Pets ok.

Cavern themed room with own entrance, kitchen & shower room. This is your own space within owner occupied property. Zip link bed, room can be twin room (2 x single beds) or double (king sized) bed. I have another adjoining accommodation that is slightly bigger with an added conservatory. There may be other guests using this space.