House holiday rentals in Isle of Portland

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.

4.99 out of 5 average rating, 259 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.

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.

4.95 out of 5 average rating, 274 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.

A stone cottage features a light green door framed by greenery. Large windows allow natural light to illuminate the entryway, while shrubs and trees create a peaceful, sheltered setting. The roofline peaks gently against a backdrop of clear blue skies.

4.96 out of 5 average rating, 107 reviews

Enchanting Manor Coach House

An elegant, relaxed home in the grounds of the Manor in this AONB with walks directly from the house. The pretty village of Winterbourne St. Martin (Martinstown) has a great pub and a super village shop both within a short walk. Close to the Jurassic Coast and spectacular country views, its the perfect place to chill after a walk, a day at the beach (approx five miles away) or visiting the many attractions in and around Dorchester. Guests have a private garden, and access to a tennis court.

A light-filled sitting room features a cozy gas fireplace framed by decorative elements. A television is positioned on a wooden unit nearby, while a soft area rug complements the seating area with patterned cushions on a beige sofa. Bookshelves are glimpsed in the background.

4.91 out of 5 average rating, 582 reviews

Tranquil Townhouse with Parking,minutes from Beach

Welcome to Weighbridge Cottage! Renovated to a high standard, this is an airy holiday home for up to 5 people plus 2 cots in central Lyme Regis and is 4 minutes easy stroll from the beach! Despite its name, Weighbridge cottage is a three story townhouse on Church Street in central Lyme Regis. It's close to everything, yet peaceful and tranquil. There's private off road parking right next to the front door. I have tried to include everything you need, toys and games, and beach stuff

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.

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.

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.

4.86 out of 5 average rating, 146 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.

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.

4.91 out of 5 average rating, 117 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.

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.

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.

The landscaped garden features a combination of grass and patio areas, with a stone pathway leading through the greenery. A small outdoor seating area is present, surrounded by tidy plants and a mature olive tree, creating a serene outdoor space.

4.98 out of 5 average rating, 197 reviews

The Stable

The Stable is a stylish converted barn for two, or a couple with a young child, set on a peaceful working farm in Broadoak. Surrounded by rolling hills and country walks, it’s just a short drive to Bridport and the Jurassic Coast. The spacious interior blends comfort with character, and outside there’s a private, landscaped garden with lawn and patio — perfect for relaxing after a day exploring Dorset.

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.

4.93 out of 5 average rating, 187 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).

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.

4.93 out of 5 average rating, 229 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.

A two-story residence features a classic facade with a prominent red front door. A car port is visible on the left, accommodating a vehicle. Large windows allow natural light to enhance the exterior, while a clear blue sky forms the backdrop.