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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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Cottage in Dorset

4.88 out of 5 average rating, 308 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...

Dec. 12 – 19

$317 CAD per night

Guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 281 reviews

The Old Apple Store, Bridport and Jurassic Coast

Our cottage is nestled in the heart of the Bride Valley close to the Jurassic Coast. This converted barn has views over our orchard. The cottage is 20 minutes drive from Dorchester and Bridport. 40 minutes to Durdle Door. Upstairs kitchen area with cooker, fridge, washing machine, lounge area with lots of books, DVD ‘s. Dining area and balcony with seating. Downstairs Large bedroom with King Size bed. Bathroom with shower. Outside pretty walled garden with seating. Min 2 night stay.

Feb. 22 – Mar. 1

$189 CAD per night

Guest favourite

Cottage in Dorset

4.97 out of 5 average rating, 539 reviews

Cute & Cosy Bothy Cottage, near Sherborne & Yeovil

The Bothy is a stylish detached cottage where you can share some Prosecco on your terrace or snuggle up beside a log fire Dating from the 1700's, our recently restored "boutique" stone cottage is in the rural historic Yetminster Conservation Area with a thatched pub, lovely local cafe & shop. It is next door to a quintessential English Heritage listed thatched cottage You are on the edge of the Dorset Area of Outstanding Natural Beauty and you have great access to the sea on the Jurassic Coast

Oct. 10 – 17

$194 CAD per night

Guest favourite

Cottage in Portland

4.81 out of 5 average rating, 118 reviews

Sea View Cottage, Portland

Sea View Cottage is part of a 200+ year old former Portland stone merchant's house just a few minutes walk from the sea, with sea views from the living room and all bedrooms and (best of all) the sea facing sun deck which gets the sun most of the day. The property sleeps 4 and has a ground floor lounge with woodstove, dining area with adjacent workspace, well equipped kitchen, and bathroom with large electric shower, first floor bedroom (double bed), and second floor bedroom (two single beds).

Apr. 6 – 13

$293 CAD per night

Cottage in Dorset

4.88 out of 5 average rating, 229 reviews

LERRET HOUSE idyllic enclosed garden, Games Room

Lerret House is close to Chesil Beach - part of the World Heritage Jurassic Coastline of Britain. The beautifully appointed cottage sleeps 5 and offers a cosy retreat with a lovely garden and nature pond, and a games room/ sun room for fun or relaxation. The area has many activities which include water sports, rock climbing and bird watching. A great base to explore all that the Jurassic Coast has to offer and a short stroll from the Cove House Inn which offers good food with stunning views.

Oct. 14 – 21

$376 CAD per night

Guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 210 reviews

Fabulous Coastal Cottage In Portland, Dorset

Welcome to our lovely, warm family holiday home. Our coastal cottage looks small from the outside but can accommodate up to eight guests and is fantastic for getaways with family or friends. With some sea views and close to the south west coastal path, the cottage is a great place to explore Portland and the surrounding area. Being a 10 minute walk from Portland Marina and Chesil Beach, it’s the perfect spot to indulge in Sailing, Bird Watching, Diving, Kayaking and other outdoor activities.

Apr. 16 – 23

$354 CAD per night

Cottage in Portland

4.89 out of 5 average rating, 129 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.

Oct. 14 – 21

$202 CAD per night

Guest favourite

Cottage in Easton

4.92 out of 5 average rating, 166 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.

Oct. 8 – 15

$175 CAD per night

Guest favourite

Cottage in Winfrith Newburgh

4.98 out of 5 average rating, 251 reviews

Bramble - 17th Century Barn Conv -enclosed garden

Bramble Barn is a beautiful 17th-century barn conversion situated down a private road just 4 miles from Lulworth Cove, Durdle Door and the Jurrasic Coast World Heritage Site. This large splendid brick barn has been converted into two identical properties creating accommodation of the highest standards. Each barn has its own enclosed garden and a south-facing terrace, ideal for eating out. Tadnoll Heath, a Dorset Wildlife Trust Reserve, lies just to the north. Ample off-road parking.

Mar. 10 – 17

$232 CAD per night

Guest favourite

Cottage in Dorset

4.92 out of 5 average rating, 135 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.

Jun. 16 – 23

$157 CAD per night

Guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 161 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!

Apr. 17 – 24

$320 CAD per night

Guest favourite

Cottage in Fortuneswell

4.98 out of 5 average rating, 186 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, 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.

Apr. 20 – 27

$226 CAD per night

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Cottage rentals with a hot tub

Cottage in Thornicombe

4.83 out of 5 average rating, 304 reviews

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

Nov. 1 – 8

$291 CAD per night

Guest favourite

Cottage in Moreton

4.95 out of 5 average rating, 151 reviews

A Stunning Dorset Thatched Cottage - Dog friendly

Apr. 1 – 8

$326 CAD per night

Guest favourite

Cottage in Dorchester

4.99 out of 5 average rating, 166 reviews

Charming Brick Cottage with a Patio and Hot Tub

Mar. 10 – 17

$396 CAD per night

Cottage in Dorset

4.83 out of 5 average rating, 238 reviews

Stillness- Connect to the Nature in the Hot Tub

Jul. 30 – Aug. 6

$317 CAD per night

Cottage in Dorset

4.78 out of 5 average rating, 64 reviews

One bedroom cottage with hot tub

Jul. 12 – 19

$215 CAD per night

Cottage in Dorchester

4.74 out of 5 average rating, 61 reviews

Nutley Farm Gatehouse

Oct. 22 – 29

$211 CAD per night

Guest favourite

Cottage in Alton Pancras

4.96 out of 5 average rating, 57 reviews

The Hideaway - sustainable hidden gem with hottub

Nov. 29 – Dec. 6

$418 CAD per night

Cottage in Sydling Saint Nicholas

4.77 out of 5 average rating, 31 reviews

Chelsea Cottage in unspoiled village West Dorset

Dec. 3 – 10

$637 CAD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Milborne Saint Andrew

4.9 out of 5 average rating, 279 reviews

Manor Farm Cottage

Nov. 7 – 14

$187 CAD per night

Guest favourite

Cottage in Dorset

4.94 out of 5 average rating, 210 reviews

Little Barn is a cosy dwelling in a remote valley

Nov. 28 – Dec. 5

$295 CAD per night

Guest favourite

Cottage in Hooke

4.93 out of 5 average rating, 225 reviews

The Little House, Hooke, Nr Bridport, West Dorset

Sep. 20 – 27

$222 CAD per night

Guest favourite

Cottage in Dorset

4.85 out of 5 average rating, 129 reviews

Idyllic hidden cottage in the heart of Bridport.

Nov. 19 – 26

$188 CAD per night

Guest favourite

Cottage in Henley

4.92 out of 5 average rating, 277 reviews

Shepherd's Cottage

Oct. 30 – Nov. 6

$126 CAD per night

Guest favourite

Cottage in Dorset

4.83 out of 5 average rating, 269 reviews

The Old Stable, Bridport - central and secluded

Aug. 28 – Sep. 4

$157 CAD per night

Guest favourite

Cottage in West Bay,Bridport

4.98 out of 5 average rating, 130 reviews

Just 100m to the beach and coast path at West Bay

Nov. 14 – 21

$309 CAD per night

Guest favourite

Cottage in Sutton Poyntz Weymouth

4.85 out of 5 average rating, 160 reviews

A peaceful retreat to rest, recharge and explore.

Jun. 3 – 10

$281 CAD per night

Private cottage rentals

Guest favourite

Cottage in Lewell

4.94 out of 5 average rating, 245 reviews

Jasmine Cottage

Sep. 25 – Oct. 2

$254 CAD per night

Guest favourite

Cottage in Okeford Fitzpaine

4.97 out of 5 average rating, 303 reviews

The Garden House Okeford Fitzpaine Dorset

Jun. 30 – Jul. 7

$249 CAD per night

Guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 155 reviews

Lovely cosy place to stay in the heart of Dorset

Oct. 23 – 30

$172 CAD per night

Guest favourite

Cottage in Dorset

4.96 out of 5 average rating, 108 reviews

Harbour's Edge Cottage - Nothe Parade, Weymouth

Feb. 6 – 13

$328 CAD per night

Guest favourite

Cottage in Bridport

5.0 out of 5 average rating, 184 reviews

Berry Farm Cottage

Feb. 12 – 19

$275 CAD per night

Guest favourite

Cottage in Waytown

4.97 out of 5 average rating, 215 reviews

Gorgeous rural cottage nr Jurassic Coast

Nov. 20 – 27

$226 CAD per night

Cottage in Dorset

4.88 out of 5 average rating, 146 reviews

Character Cottage close old harbour, beach & town

Mar. 9 – 16

$259 CAD per night

Guest favourite

Cottage in Wareham

4.99 out of 5 average rating, 243 reviews

East Walls, Wareham, Dorset

Feb. 25 – Mar. 4

$195 CAD per night

Destinations to explore