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House holiday rentals in Isle of Portland

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Top-rated house rentals in Isle of Portland

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Top Guest favourite
An open-plan living area features rustic stone walls, creating a warm ambiance. A wooden dining table is set for two, accompanied by stylish wooden chairs. A cozy seating area with a wicker chair and soft cushions invites relaxation, while large windows allow natural light to fill the space.
Home in Ryall
4.99 out of 5 average rating, 261 reviews

West Dorset cider barn with far reaching views

The grade two listed cider barn, with its own pretty terrace, has double french doors which flood the open plan living area with morning light. It is a five minute drive from the Jurassic coast with beautiful beaches and opportunities for fossil hunting . The barn has far reaching views spanning across the Marshwood Vale. This stylish and extremely comfortable new conversion is set in 11 acres of wildlife rich meadows land . It is an ideal base for exploring this beautiful part of West Dorset.

Guest favourite
The exterior of the lodge features a modern, dark wooden facade with large glass doors that open into the main living area. A spacious patio area is surrounded by landscaped gardens, with decorative plants and seating arrangements for relaxation.
Home in Leigh
4.95 out of 5 average rating, 277 reviews

Luxurious rural retreat

The Lodge at Willen Farm is a beautiful single level converted barn on the outskirts of the quiet village of Leigh, just 4 miles from the town of Sherborne in Dorset. The Lodge provides the perfect location for a relaxing escape to the rural countryside, yet just 40 minutes from the fabulous Jurassic coastline. Spacious accommodation with two double bedrooms, one with en-suite shower/toilet and a separate bathroom. Contemporary style with an outside patio area. Parking and a small garden area.

Guest favourite
An expansive view of the sea captures the vibrant hues of sunset blending into the sky. The foreground features charming stone houses, while the calm ocean reflects the warm colors of twilight, creating a serene coastal scene.
Home in Dorset
4.94 out of 5 average rating, 105 reviews

Charming Portland house with sea and sunset views

Welcome to our renovated Dorset getaway. Our Portland stone house is 5 minutes walk from Chesil Beach and 20 minutes walk to the Weymouth & Portland National Sailing Academy. The Isle of Portland is an idyllic spot to relax with stunning sea views or base yourself to explore the many activities in the area: walking, coasteering, horse riding, sailing, water sports, alpacas etc. The house is perfect for a self catering getaway but there are great restaurants a short walk away.

Top Guest favourite
A cozy sitting room features a combination of exposed stone and modern decor. A plush dark sofa and green armchair are positioned around a wooden coffee table. Natural light enters through the large window, which is dressed with white shutters. A television is mounted on the wall.
Home in Lyme Regis
4.99 out of 5 average rating, 272 reviews

Grand Cosy Stay by the Seaside in Lyme Regis

‘Waterside’ sits on the River Lym, originally built in the 1800’s, inspired by France in the busy port trading days of Lyme Regis. This well photographed house commands its place along this notable stretch of water. Completely and beautifully renovated in early 2021. Enjoy views from the middle and top floor overlooking the 17th century Gosling Bridge and the ‘Lynch’ where the waterway divides to service the town mill. 4-minute walk to the beach, artisan shops & high street.

Top Guest favourite
A tall stone monument is prominently situated atop a grassy hill, surrounded by lush greenery. A weathered wooden signpost stands in the foreground, pointing in two directions. The sky features scattered clouds and clear blue sections, creating a bright outdoor scene.
Home in Dorset
4.97 out of 5 average rating, 149 reviews

Cheerful one bedroom home in the heart of Dorset

A great base for exploring Dorset and centrally-located. This newly decorated self contained 1 bedroom annexe has a fully equipped kitchen & in the county town of Dorchester, the birth place of Thomas Hardy. It is a perfect base to explore the beautiful countryside and Jurassic coast! The town’s amenities are only a short walk away including the new Brewery Square development. Complimentary tea and coffee also provided. Please note, we are unable to accommodate children

Guest favourite
The living area features a modern grey sectional sofa adorned with patterned cushions. A wooden coffee table sits on a blue area rug. Natural light enters through a large window, while a mounted TV and decorative wall elements enhance the stylish design.
Home in Dorset
4.85 out of 5 average rating, 239 reviews

Olly's Retreat

Step inside Olly's and you'll be impressed by the modern and stylish interior and the benefit of a sunny private courtyard. Accommodation consists of a large open plan modern living space, with integrated kitchen. The large bathroom with power shower is also located on the ground floor. Upstairs two generous bedrooms, one with a king size bed and the other twin beds. The property sleeps four and we also accept dogs (however please do not leave them alone in the property)

Superhost
A living area features light-colored furniture, including a cozy sofa adorned with decorative pillows. A flat-screen television sits on a dark wooden unit. Artwork depicting a sailboat and a wooden oar add character to the walls. Natural light enters through a window with light shades.
Home in Dorset
4.84 out of 5 average rating, 148 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
The exterior of a charming farmhouse is displayed, featuring a thatched roof and stone walls. A fenced garden surrounds the property, with a patio area furnished with a dining table and chairs. Lush green grass enhances the rural atmosphere.
Home in Bettiscombe
4.92 out of 5 average rating, 118 reviews

Beautiful farmhouse in Dorset

Sunnyside at Waterhouse Farm is a spacious farmhouse on our working farm in West Dorset, surrounded by fields and woodland. The house has a fenced garden and easy access to miles of local footpaths. Upstairs are two large ensuite bedrooms: one with a king bed, the other with either three singles or a double and single. Downstairs features a cosy sitting room with wood burner, an open-plan kitchen and dining area, plus a utility room with cloakroom.

Top Guest favourite
An open-plan living area features a spacious bed adorned with a floral-patterned duvet. A comfortable sofa and coffee table are visible, with bifold doors leading to a terrace. Natural light fills the room, complemented by a small table with fresh flowers and a map on the wall.
Home in Wynford Eagle
4.92 out of 5 average rating, 278 reviews

Swallows Return - Alpacas-Gardens-Brook-Tennis

Nestled in an area of Outstanding Natural Beauty, Wynford Eagle is one of West Dorset's hidden gems. Swallows Return is a cosy studio retreat, a haven for peace and relaxation which opens out onto a large terrace with stunning views of the valley, 8 acres of grounds and gardens and beautiful alpacas. A great base to explore Dorset, situated just 15 minutes from the Jurassic coastline and all this incredible area has to offer.

Top Guest favourite
A single-story lodge is surrounded by a spacious green lawn, featuring large glass doors that brighten the interior. Tall trees and hedges provide natural privacy, while rolling fields rise in the background under a clear blue sky.
Home in Cruxton
4.98 out of 5 average rating, 214 reviews

Kingfisher Lodge with Private Riverbank

A beautiful Lodge set in 7.5 acres with its own riverbank, situated down a Dorset country lane. Set amongst fields, the tranquil, peaceful surroundings make the accommodation perfect for those who want to get away. Devoid from light pollution, the sweeping skies make it an ideal spot for star gazing. The Jurassic Coast is only a short drive, with beautiful coastal walks. A perfect break!

Guest favourite
A cozy bedroom features a large bed adorned with red accents and intricately folded towel designs. Two wooden nightstands flank the bed, and a wooden dresser with a mirror is situated nearby. The wall is decorated with a floral wallpaper, creating a cheerful atmosphere.
Home in Easton
4.93 out of 5 average rating, 188 reviews

Top To Bottom beautiful cottage heart of Easton

My place is close to great views, restaurants and dining. You’ll love my place because of the location, the people, the outdoors space, and the neighbourhood. My place is good for couples, families (with kids), big groups, and furry friends (pets).

Top Guest favourite
A charming cottage exterior features a light-colored facade with a slate roof, framed by greenery and stone details. The entrance, highlighted by a classic columned portico, is complemented by two windows on either side, providing a welcoming and quaint appearance.
Home in Dorset
4.93 out of 5 average rating, 230 reviews

April's Cottage, sea views close to Chesil Beach

Escape from it all in this little cosy character cottage crammed with history and home comforts including own parking right outside your front door. Located in the heart of the Jurassic coast, moments from Chesil Beach, local shops, pubs and cafes.

Popular amenities for Isle of Portland house rentals