
Cottage vacation rentals in Isle of Portland
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Top-rated cottage rentals in Isle of Portland
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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...

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.

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.

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.

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.

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 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.

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.

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.

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.

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.

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.
Popular amenities for Isle of Portland cottage rentals
Cottage rentals with a hot tub

1 Bed in Osmington (82098)

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

Cherry Lodge

Romantic Retreat with hot tub

A Stunning Dorset Thatched Cottage - Dog friendly

Dreamwood - Woodland Cottage with Private Hot Tub

Charming Brick Cottage with a Patio and Hot Tub

The Hideaway - sustainable hidden gem with hottub
Pet-friendly cottage rentals

Barn conversion set in farmland near to the beach

Grove Farm Cottage-historic Cottage near Sherborne

Marwells Farm Cottage

Cosy Purbeck Cottage on the Jurassic Coast

The Little House, Hooke, Nr Bridport, West Dorset

Sunflower House

Brushwood Cottage; walking, beaches & Corfe Castle

Tea Room Holiday Cottage
Private cottage rentals

Thatched Cottage by the Beach

Jasmine Cottage

Stylish country cottage close to Jurassic Coast

Pilgrims Cottage-Luxury Grade 1 Listed cottage

Blackbird Cottage, Dorset with Cosy Wood Burner

18th Century Cottage Annex - nearJurassic Coast

Cheerful 1960's cottage with fireplace

No1. The Courtyard, Clyffe House
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- New Forest national park
- Paultons Park Home of Peppa Pig World
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