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Cottage vacation rentals in Isle of Portland

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Top-rated cottage rentals in Isle of Portland

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An open-plan lounge area displays a wood-burning fireplace set against a rustic stone hearth, with shelves featuring decorative items. Two low sofas are arranged for seating, accompanied by a colorful accent chair. Natural light enters through a window, illuminating the soft area rug.

Cottage in Dorset

4.88 out of 5 average rating, 348 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...

A charming thatched cottage features a traditional exterior with stone and whitewashed walls. The front door, framed by a small potted plant, is accented by decorative flower boxes beneath square windows. Surrounding greenery provides a serene backdrop, enhancing the cottage's rural appeal.

Cottage in West Lulworth

4.92 out of 5 average rating, 123 reviews

Thatched Cottage by Lulworth Cove & Durdle Door

A beautiful thatched chocolate box cottage on the breathtaking Dorset Jurassic Coast. A quintessential Lulworth Grade II listed property dating back to 1750, ideally situated within a very short walk of Lulworth Cove. Perfect for those looking for a rural retreat in one of the country's most appealing coastal villages. A fabulous spot for family holidays and breaks exploring the area by foot, paddle and bike, the cottage is also within easy reach of local towns and outstanding country pubs.

A charming stone cottage is surrounded by lush greenery and various colorful flowering plants. A small white table and two chairs are placed outside, inviting guests to enjoy the garden view. The cottage features a traditional door framed by vibrant foliage.

Cottage in Dorset

4.97 out of 5 average rating, 625 reviews

Cute, Cosy & Stylish Bothy Cottage, near Sherborne

Stylish, Comfortable & Quirky - “Top 10 Dorset Airbnb” (Conde Nast Traveller) in a “Top 50 UK Village” (Sunday Times). The Bothy is a detached stone cottage where you can share some free Prosecco on your private terrace. It is in the rural historic Yetminster Conservation Area with a thatched pub, café & shop. It is next door to a quintessential "Chocolate Box" thatched cottage. You are on the edge of the Dorset Area of Outstanding Natural Beauty with good access to the sea & Jurassic Coast.

Top guest favorite

A stone fireplace with a log burner is positioned against a textured stone wall, providing warmth and ambiance. A festive Christmas tree adorned with lights and decorations adds a cheerful touch. A decorative rug with a holiday message is placed in front of the fireplace.

Cottage in Easton

4.93 out of 5 average rating, 199 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.

The exterior view of the converted barn is presented, showcasing the stone structure surrounded by lush greenery. A gravel driveway leads to the property, with an outdoor seating area visible. Neat hedges outline the garden, offering a sense of privacy amid the scenic countryside.

Cottage in Dorset

4.94 out of 5 average rating, 250 reviews

Little Barn is a cosy dwelling in a remote valley

Little Barn is located in a remote valley between Upwey and Portesham near Weymouth in Dorset A converted Barn with a modern open plan interior. An adequate garden with Outdoor furniture and BBQ with an external secure store for bicycles etc. The area is good for walking (dogs welcome), many footpaths line the surrounding countryside. Hardy's monument is situated a few miles away. The area offers good cycling both on and off road. Good access to the Dorset coastline which is a short drive away.

A cottage made of natural stone is surrounded by lush greenery and colorful flowers. A spacious balcony extends over the entrance, providing an outdoor area to enjoy the views. The sun illuminates the property, enhancing its inviting presence in the serene landscape.

Cottage in Morcombelake

4.95 out of 5 average rating, 421 reviews

Romantic hillside hideaway with outstanding views

A unique and romantic hideaway, Quarryman's Cottage is dinner on the roof terrace watching the sunset over Lyme Bay & Charmouth, stargazing from the luxury freestanding bath, epic views from the double shower, reading under the old oak tree, BBQ's & firepits, leisurely walks to The Anchor at Seatown via Golden Cap or the coastal path, the sound of birdsong, the glimpse of a deer, curling up in front of the wood burner in winter. It is a tranquil & heavenly escape from the bustle of daily life.

An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.

Cottage in Osmington

4.87 out of 5 average rating, 136 reviews

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

A cozy living area features a brown leather sofa with yellow cushions. A star-shaped decoration and a small potted plant are displayed nearby. Light filters through a window with white shutters, and a framed picture of a lighthouse adorns the wall above the furnishings.

Cottage in Portland

4.87 out of 5 average rating, 164 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.

A cozy lounge area features a rustic stone fireplace with a log burner, surrounded by soft seating. A plush rug lies on the wooden floor, and framed pictures are hung on the walls. A staircase leads to the upper level.

Cottage in Easton

4.92 out of 5 average rating, 220 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.

A stone cottage is surrounded by a small fence and a well-maintained garden. Large windows provide views from the ground floor, and patio doors lead to an outdoor seating area. The structure features traditional architecture with a mix of modern elements and greenery nearby.

Cottage in Fortuneswell

4.89 out of 5 average rating, 115 reviews

Cove Garden Grade II Cottage

Magical sunsets and magnificent coastal walks. Stop the clock relax and enjoy all that this little haven on the Jurassic coast has to offer. Something for everyone from chilling and reading to water sports such as sailing, kite surfing and paddle boarding. There are plenty of local pubs, restaurants and cafes to choose from too. Some of the best in walking distance. The local art and music scene is very established. This is a great spot to explore the Dorset coast and venture inland.

A serene coastline is depicted at sunset, with the sun gently descending towards the horizon. The soft gradient of colors in the sky reflects on the quiet water, while a pebbled beach runs along the foreground, providing a peaceful natural setting.

Cottage in Dorset

4.9 out of 5 average rating, 167 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.

Top guest favorite

A view of Maidenwell Cottage from the garden, showcasing a landscaped area with palm trees and vibrant flowers. The cottage's exterior features a blue door and a stone wall, framed by greenery that enhances the inviting outdoor space.

Cottage in Fortuneswell

4.99 out of 5 average rating, 273 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.

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Popular amenities for Isle of Portland cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A spacious outdoor area features a large hot tub with contoured seating, surrounded by greenery. A brick patio extends across the area, providing ample room for relaxation and outdoor furniture. A well-maintained lawn is visible in the background, enhancing the outdoor setting.

Cottage in Sandford

4.87 out of 5 average rating, 15 reviews

Cherry Lodge

A private outdoor area features a wooden hot tub surrounded by a pebble path and manicured shrubs. A small table with two chairs sits nearby, illuminated by string lights overhead. The rustic building's stone facade adds character to the tranquil setting.

Cottage in Somerset

4.85 out of 5 average rating, 91 reviews

Romantic Retreat with hot tub

Top guest favorite

The charming thatched cottage features a wooden roof terrace surrounded by lush greenery. Stonework and a blue door create a rustic appearance, while ample sunlight illuminates the exterior. A gravel pathway leads to the entrance, framed by trees and shrubs.

Cottage in Moreton

4.96 out of 5 average rating, 181 reviews

A Stunning Dorset Thatched Cottage - Dog friendly

A glamping lodge is showcased with a curved wooden exterior and a private patio. A picnic table is situated on the deck, accompanied by a hot tub near the fenced area. Lush green grass surrounds the lodge, and clear skies provide a bright backdrop.

Cottage in Blandford Forum

4.83 out of 5 average rating, 355 reviews

Ranmoor Estate - Starling Lodge - Hot Tub & A/C

An open-plan kitchen features a central island with bar stools, complemented by a wooden dining table set for a meal. Modern appliances, including a double oven and a large refrigerator, are visible, while natural light brightens the space through the large windows.

Cottage in Dorset

4.85 out of 5 average rating, 61 reviews

NEW - Coastal cottage in Lyme Regis, hot tub

A thatched farmhouse is set amidst a lush green lawn, featuring vibrant flowerbeds along the front. A well-maintained garden includes wooden outdoor furniture, offering a serene space for relaxation. Large windows allow natural light to enhance the inviting exterior of the cottage.

Cottage in Dinnington

4.95 out of 5 average rating, 536 reviews

The Cottage, Parsonage Farmhouse with hot tub

The exterior of the cottage features a charming brick façade complemented by a slate roof. A hot tub is positioned near a patio set with a table and chairs under an umbrella, providing a space for outdoor dining. Lush greenery and fields are visible in the background.

Cottage in Dorchester

4.98 out of 5 average rating, 208 reviews

Charming Brick Cottage with a Patio and Hot Tub

A spacious living area is showcased, featuring a comfortable gray sofa, stylish armchairs, and a wooden coffee table. A flat-screen TV is mounted on the blue wall. Large glass doors open to reveal expansive views of the outdoor space, inviting natural light into the room.

Cottage in Alton Pancras

4.95 out of 5 average rating, 85 reviews

The Hideaway - sustainable hidden gem with hottub

Pet-friendly cottage rentals

A cozy living area features a wood burner set into a simple mantel, complemented by a glass coffee table with wooden legs. Two colorful armchairs, one yellow and one teal, are arranged around the space, with natural light streaming through the windows adorned with potted plants.

Cottage in Dorset

4.93 out of 5 average rating, 157 reviews

A Charming Cottage, Just a Moment from the Beach

A charming garden path leads through vibrant flowers, including pink fuchsias and white hydrangeas, bordered by greenery. A gravel pathway curves gently towards a seating area with bistro-style tables and chairs, shaded by an umbrella, offering a tranquil outdoor retreat.

Cottage in Somerset

4.93 out of 5 average rating, 338 reviews

Cottage in the heart of Montacute

Cottage in Bridport

4.9 out of 5 average rating, 123 reviews

5* Cottage on Chesil Beach Dorset Jurassic Coast

A charming stone cottage features soft hues and traditional architecture. A light blue front door adds a welcoming touch, while neatly trimmed hedges frame the entrance. Multiple windows invite natural light, highlighting the warm stone exterior against a clear sky.

Cottage in Dorset

4.91 out of 5 average rating, 156 reviews

Quaker Cottage

A rustic log burning stove is positioned beside a charming stone wall, offering a cozy focal point. A woven rug covers the floor, leading to a dining area with a light-colored table and soft seating, inviting relaxed gatherings.

Cottage in West Coker

4.93 out of 5 average rating, 181 reviews

Little Gem Somerset Cottage

The exterior of The Parlour cottage is depicted, featuring a brick façade with large windows that allow natural light to fill the interior. A spacious gravel area surrounds the cottage, providing convenient access. The tranquil countryside can be glimpsed in the background under a clear blue sky.

Cottage in Duntish

4.95 out of 5 average rating, 164 reviews

The Parlour, Duntish Mill Farm, EV Charging

Top guest favorite

A tranquil bedroom features a metal framed bed adorned with soft, patterned linens. Natural light enters through dual windows dressed in floral curtains. A classic wooden chair and a dresser complement the space, which is finished with a cozy woven rug and a decorative ceiling light.

Cottage in Henley

4.93 out of 5 average rating, 352 reviews

Shepherd's Cottage

Top guest favorite

A bright and inviting bedroom features a spacious king-sized bed dressed in soft linens with decorative cushions. A rustic chest of drawers complements the decor. Natural light filters through a window adorned with delicate curtains, enhancing the warm atmosphere.

Cottage in Stourpaine

4.95 out of 5 average rating, 129 reviews

Tudor Rose Luxury thatched cottage Dorset.

Private cottage rentals

The exterior of a single-storey barn conversion is featured, showcasing a well-maintained grassy area and a path leading to a wooden door. A rustic brick facade complements the surrounding greenery and trees, providing a serene countryside view.

Cottage in Bettiscombe

4.91 out of 5 average rating, 124 reviews

Pigs' House - cosy, rural cottage in West Dorset

The exterior of the eco-friendly lodge showcases a wooden façade with a triangular feature window. A cozy patio area is visible, furnished with a table and four chairs, surrounded by lush greenery, providing a serene outdoor space.

Cottage in Dorset

4.95 out of 5 average rating, 164 reviews

Cosy, quirky 2 bdrm ecolodge close to town & beach

A charming cottage with a thatched roof is nestled in a leafy garden. Colorful flowerpots enhance the entrance, while greenery surrounds the property. The bright blue sky provides a serene backdrop for this quaint retreat.

Cottage in Colehill

4.88 out of 5 average rating, 245 reviews

Brightside Cottage

The exterior of a refurbished mews cottage is showcased, featuring a brick façade and large arched windows. A stable door is visible, while the cobblestone path in front offers access to the entrance. Dark double doors lead to a garage, adding character to the property.

Cottage in Dorset

4.92 out of 5 average rating, 143 reviews

Fantastic centrally located mews cottage

The bedroom features a spacious bed dressed in a checkered duvet. Two bedside tables with lamps are positioned on either side. Above the bed, two framed prints of abstract botanical designs are displayed on the light-colored wall.

Cottage in Dorset

4.95 out of 5 average rating, 148 reviews

Quayside Cottage- Stone’s Throw From Poole Quay

Top guest favorite

The historic flint cottage is framed by lush greenery, including climbing plants and surrounding shrubs. Its attractive stone facade features multiple windows, allowing natural light to filter through. A welcoming entrance is visible, hinting at the charm of the interior.

Cottage in Thorncombe

4.96 out of 5 average rating, 222 reviews

Peaceful cottage in West Dorset - AONB

A tree trunk is adorned with soft glowing fairy lights, creating a warm ambiance in the garden. In the background, a charming summer house is visible, framed by lush green foliage and illuminated by the gentle light.

Cottage in Beaminster

4.92 out of 5 average rating, 138 reviews

Cosy Cottage in West Dorset – Near Beaches & Walks

A cozy living area is furnished with light-colored sofas, complemented by a wooden coffee table. A soft rug covers the carpeted floor, and a fireplace serves as a focal point. Natural light is provided through nearby windows, enhancing the welcoming atmosphere.

Cottage in Langton Matravers

4.91 out of 5 average rating, 392 reviews

Chapel Cottage

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