Vacation rentals in Isle of Portland

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Top-rated vacation rentals in Isle of Portland

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Guest favorite

Townhouse in Dorset

4.95 out of 5 average rating, 130 reviews

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

CLOUD9 was designed with extreme love by our family 🧡🌿 Original features with a twist of vintage & new decor 😊 Frontroom/Dining Room area, kitchen with downstairs toilet & door to enclosed patio. 1st Floor with a spacious shower room. Peacock 🦚 bedroom. Blossom bedroom🌸 bay window with sea views 🌊 Attic room twin bedroom, velux windows with sea views. All furnishings are comfy, cosy 🧡 homely & happy 🙂 The beach 🌊 is 5 minutes bimble, a local co-op, fish & chip shop & pubs🐟 😊

Guest favorite

Cottage in Easton

4.93 out of 5 average rating, 177 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 favorite

Condo in Dorset

4.9 out of 5 average rating, 397 reviews

1 Bed Apartment Portland near Weymouth Dorset

The apartment is located in Portland near to a Portland Port and 5 miles to Weymouth 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 shower.There is a sofa bed suitable for young children. Parking is nearby but free parking is available in the street.

Superhost

Cottage in Portland

4.88 out of 5 average rating, 150 reviews

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.

Guest favorite

Cottage in Easton

4.92 out of 5 average rating, 192 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.

Guest favorite

Cottage in Dorset

4.92 out of 5 average rating, 153 reviews

Chesil Cove Holiday Cottage

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

Guest favorite

Home in Dorset

4.96 out of 5 average rating, 113 reviews

Chesil Cove, Portland's jewel

Detached house in beautiful Chesil Cove, literally a pebble's throw from the sea. Perfectly situated for divers, sailors, walkers and anyone who enjoys beach life. Private parking for 2/3 cars. Pubs, restaurants and takeaways all in easy walking distance. Special features for divers and watersport fans include a hot water outside shower, lockable shed for stowing gear and drying racks for wetsuits. Well behaved dogs welcome. Dog towels and a cosy alcove for their bed available.

Guest favorite

Cottage in Dorset

4.97 out of 5 average rating, 190 reviews

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!

Guest favorite

Cottage in Fortuneswell

4.99 out of 5 average rating, 231 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 favorite

Bungalow in Dorset

4.96 out of 5 average rating, 110 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this is 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. A 20 min bus ride to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem.

Guest favorite

Vacation home in Easton

4.95 out of 5 average rating, 133 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.

Guest favorite

Guest suite in Dorset

4.84 out of 5 average rating, 170 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