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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, 355 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 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, 206 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.

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

4.89 out of 5 average rating, 174 reviews

Chesil Cove Holiday Cottage

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

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

4.95 out of 5 average rating, 257 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, 437 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.

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, 172 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 sunlit courtyard garden features stone paving and a wooden table set with two chairs. Planters filled with greenery surround the area, creating a tranquil spot. A plaid blanket drapes over one chair, inviting relaxation among the plants and flowers.

Cottage in Langton Matravers

4.9 out of 5 average rating, 250 reviews

Cosy Cottage in Rural Hamlet on the Jurassic Coast

Quirky, Cozy Cottage. Perfect for a winter/summer break. Coal/Wood burner and a Super-King Size Bed. Located in Acton, A small tranquil hamlet, The cottage is surrounded by fields and located right on the South West Coast Path. Incorporating breath-taking views from all around. Everything is on your doorstep! Walkable is the Square and Compass, The Kings Arms in Langton, Dancing Ledge, Seacombe, Chapmans Pool, Dinosaur Footprints, The South West Coast Path, Swanage and Studland Beaches.

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, 227 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

4.88 out of 5 average rating, 125 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.

Top guest favorite

The exterior of the cottage is showcased, highlighting a charming wooden structure adorned with climbing foliage. A gravel driveway leads up to the entrance, framed by neatly arranged planters. A wooden fence enhances the privacy of the property, complemented by young trees.

Cottage in Bridport

4.99 out of 5 average rating, 233 reviews

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.

The exterior of the cottage features natural stone walls and a light blue front door, inviting guests inside. The garden area includes greenery and bushes, enhancing the entrance. Two windows on the upper level allow natural light to brighten the façade.

Cottage in Dorset

4.96 out of 5 average rating, 228 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!

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, 285 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

An exterior view showcases a spiral staircase leading to a balcony, surrounded by a light blue building. A private hot tub sits on a paved area below, with surrounding fencing providing privacy. Natural stone and wooden elements add to the contemporary style.

Cottage in Osmington

5 out of 5 average rating, 7 reviews

1 Bed in Osmington (82098)

A glamping lodge is situated on a wooden deck, featuring a large picnic table set with drinks. A hot tub is visible nearby, surrounded by a wooden railing. Lush green grass and trees form a scenic backdrop under a clear blue sky.

Cottage in Blandford Forum

4.83 out of 5 average rating, 445 reviews

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

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

4.75 out of 5 average rating, 16 reviews

Cherry Lodge

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

4.95 out of 5 average rating, 183 reviews

A Stunning Dorset Thatched Cottage - Dog friendly

Top guest favorite

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, 210 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

4.94 out of 5 average rating, 89 reviews

The Hideaway - sustainable hidden gem with hottub

A wood-fired hot tub sits on raised decking, surrounded by trees and wildflowers. Soft lighting from overhead string lights adds a warm glow to the evening scene. In the background, the converted barn is visible, with illuminated windows suggesting a cozy interior.

Cottage in Hazelbury Bryan

3 Bed in Hazelbury Bryan (COWOB)

Top guest favorite

A heated swimming pool with a vibrant blue surface occupies the center of the outdoor space. Surrounding the pool are sun loungers and a hot tub, with a stone patio featuring a decorative table and chairs. Lush greenery and the thatched cottage are visible in the background.

Cottage in Dorset

5 out of 5 average rating, 22 reviews

17thC thatched cottage in farming hamlet

Pet-friendly cottage rentals

A spacious sitting room features soft furnishings in calming shades, including two blue sofas adorned with colorful cushions. A light wood coffee table sits in the center, and a woven rug complements the natural wood flooring. Exposed stone walls and wooden beams enhance the rustic charm.

Cottage in Charmouth

4.95 out of 5 average rating, 185 reviews

Barn conversion set in farmland near to the beach

The exterior of the cottage features a charming pink facade with a stone-clad entrance. A small round table with two green chairs allows for outdoor seating. The garden is adorned with various plants and flowers, enhancing the inviting atmosphere of the cottage entrance.

Cottage in Chetnole

4.9 out of 5 average rating, 197 reviews

Grove Farm Cottage-historic Cottage near Sherborne

A sweeping aerial view of Lulworth Cove captures the crescent-shaped beach with blue waters, dotted with boats. The surrounding coastline features lush green hills and rocky cliffs, with bright blue skies above, conveying a sense of serenity and natural beauty.

Cottage in West Lulworth

4.92 out of 5 average rating, 172 reviews

Lulworth Cove - Jurassic Coast - Sleeps up to 8

Top guest favorite

The traditional cottage features a thatched roof and rustic stone walls, surrounded by a vibrant garden lush with flowers and greenery. A wooden bench is placed in the foreground, inviting relaxation amidst the scenic backdrop of blooming plants and shrubs.

Cottage in Bridport

4.95 out of 5 average rating, 107 reviews

Strongate Cottage nr Bridport Dorset Rural Retreat

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 Dorchester

4.93 out of 5 average rating, 361 reviews

Shepherd's Cottage

A traditional cottage is depicted surrounded by lush greenery and flowering plants. The stone façade is complemented by a well-maintained front garden, while a pathway leads to the entrance. Blue skies and scattered clouds enhance the peaceful rural setting.

Cottage in Dorset

4.78 out of 5 average rating, 143 reviews

Tranquil two bedroom cottage with rural views.

A country-style kitchenette is presented with a farmhouse sink and wooden countertop. Natural light enters through multiple windows adorned with potted flowers. A microwave and task lighting from a lamp enhance the cozy atmosphere.

Cottage in Worth Matravers

4.91 out of 5 average rating, 182 reviews

Tea Room Holiday Cottage

A charming cottage is visible in warm-toned brick, featuring a sloping red roof and a small tower. A spacious driveway leads to the entrance, framed by bushes and outdoor seating. Clear blue skies create a serene backdrop, enhancing the cottage's welcoming appearance.

Cottage in Duntish

4.96 out of 5 average rating, 116 reviews

HayMow, Duntish Mill Farm with EV Charging

Private cottage rentals

The exterior of the cottage features a charming stone façade with a thatched roof. A wooden door is surrounded by multiple windows. Lush greenery is present in the garden, along with a small patio area furnished with a dining set.

Cottage in Dorset

4.97 out of 5 average rating, 72 reviews

Thatched Cottage by the Beach

A private garden features a round table surrounded by four chairs, set on a stone patio. Lush greenery and flowering plants border a well-maintained lawn, while a rustic shed is visible in the background under a clear blue sky dotted with clouds.

Cottage in Lewell

4.94 out of 5 average rating, 298 reviews

Jasmine Cottage

A traditional two-story cottage in a light pastel shade is shown, featuring a blue front door and several windows on the gabled facade. A peaceful street is visible in front, and the surrounding area includes a grassy slope leading to additional structures.

Cottage in Dorset

4.72 out of 5 average rating, 18 reviews

Dolphin Cottage, Chesil Beach

Cottage in Chideock

4.95 out of 5 average rating, 100 reviews

Walk to beach and good pubs. Parking.

The charming exterior of a Grade 1 listed cottage is presented, showcasing a white facade with traditional windows. Stone pathing and stone planters filled with greenery add to the welcoming appearance. The neighboring cottages feature historic architectural details, enhancing the village's character.

Cottage in Cerne Abbas

4.96 out of 5 average rating, 79 reviews

Pilgrims Cottage-Luxury Grade 1 Listed cottage

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

4.97 out of 5 average rating, 229 reviews

Peaceful cottage in West Dorset - AONB

Cottage in Beaminster

4.92 out of 5 average rating, 145 reviews

Cosy Cottage in West Dorset – Near Beaches & Walks

Top guest favorite

An open plan living area features natural wood flooring, a round dining table with four chairs, and a large sofa bathed in afternoon light. A wall-mounted TV is visible, alongside large windows that allow for ample sunlight, enhancing the overall space.

Cottage in South Perrott

4.81 out of 5 average rating, 138 reviews

18th Century Cottage Annex - nearJurassic Coast

Destinations to explore