Cottage vacation rentals in Isle of Portland

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Top-rated cottage rentals in Isle of Portland

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Superhost
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...

Top guest favorite
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, 644 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.

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
4.92 out of 5 average rating, 209 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
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, 258 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.

Guest favorite
A private, enclosed garden is displayed featuring a brick pathway that leads to the cottage. Lush greenery surrounds the space, complemented by potted plants and a small grassed area. Outdoor seating is positioned for relaxation, and a pond adds charm to the tranquil setting.
Cottage in Wyke Regis
4.82 out of 5 average rating, 128 reviews

Coastal Hideaway, Weymouth/Portland cosy cottage

The cottage is nestled in the lovely village of Wyke Regis, tucked away just off the quiet Old High street and close to both Weymouth and Portland. Perfect for small families/couples + dogs. Within easy walk of small beaches, coastal walks and amenities such as dog friendly pub, cafes, Tesco Express and chips shop/takeaways. Portland harbour is a mere 2 miles away as is the World famous Chesil Beach which forms part of the Jurassic coast. SWC Path is minutes walk away, perfect for a stop over.

Guest favorite
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, 445 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.

Superhost
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
4.86 out of 5 average rating, 153 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.

Superhost
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
4.86 out of 5 average rating, 174 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
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
4.91 out of 5 average rating, 232 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.

Superhost
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, 130 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
An open plan living area features high wooden beams and a log burner. A cozy seating area is arranged beside a wooden dining table. Above, a loft with a king-size bed can be seen, with thick curtains for privacy. Decorative elements are displayed on the walls.
Cottage in Corfe Castle
4.99 out of 5 average rating, 271 reviews

Cottage by the Common, Corfe Castle

The Cottage is an open plan building next to the entrance to Corfe Common in a tranquil setting. Downstairs there is a King-size bed & upstairs there are 2 single beds . Sleeping areas are open plan but have thick curtains that can be drawn to create a private and cosy space. Downstairs has Wet-room with sink & separate toilet & sink New Kitchen WiFi Log burner and 2 free basket of logs South facing Patio Parking 2 cars 5 mins walk to Corfe Village Pets welcome.

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, 236 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.

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