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Vacation rentals in Isle of Portland

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Top-rated vacation rentals in Isle of Portland

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Cottage in Dorset

4.88 out of 5 average rating, 307 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...

Jan. 23 – 30

$321 CAD per night

Guest favourite

Condo in Dorset

4.9 out of 5 average rating, 313 reviews

1 Bed Apartment Weymouth and Portland, Dorset

The apartment is located in Portland 5 miles to Weymouth The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks and cycle routes to Weymouth. It is a one bedroom apartment.There is a small Beach 30 seconds of the doorstep and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric shower.There is a sofa bed suitable for young children. Parking is nearby but free parking is available in the street.

Dec. 12 – 19

$115 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. 17 – 24

$208 CAD per night

Guest favourite

Cottage in Easton

4.92 out of 5 average rating, 165 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.

Jul. 2 – 9

$174 CAD per night

Guest favourite

Tiny homes in Portland

4.94 out of 5 average rating, 190 reviews

Coast - White Stones Studios

Come and enjoy our new and unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

Nov. 19 – 26

$155 CAD per night

Guest favourite

Cottage in Dorset

4.93 out of 5 average rating, 133 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. 9 – 16

$164 CAD per night

Guest favourite

Cottage in Dorset

4.97 out of 5 average rating, 159 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!

Nov. 27 – Dec. 4

$279 CAD per night

Apartment in Fortuneswell

4.81 out of 5 average rating, 144 reviews

The Cobblers retreat

Upstairs open plan flat with separate wet room. Set at the back of our house with a private entrance in the lane. The space is a modern new build with a kitchenette Microwave,kettle,toaster NO OVEN OR HOB .The flat has free WIFI and a modern smart tv. The heating is provided via central heating linked to the main house . Bikers and surfers are welcome, we can store your pride and joy in additional space by arrangement. We can only cater for 2 guests. Dogs are welcome

Oct. 19 – 26

$180 CAD per night

Guest favourite

Cottage in Fortuneswell

4.98 out of 5 average rating, 183 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.

Sep. 17 – 24

$225 CAD per night

Tiny homes in Dorset

4.84 out of 5 average rating, 238 reviews

Cove Holiday Park - Pod 2

Pod 2 has a modern, fully equipped kitchen, bathroom, sofa, TV and drop-down double bed. You can sit in bed with a view of the sea or chill on the deck with a glass of wine on a sunny evening. Our Pods come with bed linen and towels included. -Fantastic elevated sea views from the top level of Park (The view is shown in the images) -Large decking with outside seating -Innovative pull-down double bed and fold away sofa -No pets

Jul. 19 – 26

$140 CAD per night

Guest favourite

Cottage in Dorset

4.95 out of 5 average rating, 101 reviews

Spacious Family Cottage with Sea Views of Chesil

Chesil View Cottage is situated on the Isle of Portland, with spectacular views of the acclaimed Chesil Beach. A traditional style terraced Cottage, with sea views throughout the house. Perfect for families, friends and couples. Take a look at our Instagram page for more seasonal photos https://instagram.com/chesilview_cottage_holidaylet?utm_medium=copy_link

Apr. 26 – May 3

$264 CAD per night

Guest favourite

Cottage in Dorset

4.85 out of 5 average rating, 352 reviews

Character cottage close to beach

Spacious and beautiful house 5 min walk to Chesil Beach. Free superfast wi-fi, well equipped kitchen including dishwasher and a cosy log burner in living room. Scandi style décor. Netflix and smart TV. Right in heart of Fortuneswell, Portland with some shops, pubs and restaurants close by. 10-15 min drive from Weymouth. Great for couples.

Nov. 4 – 11

$222 CAD per night

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

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Popular amenities for Isle of Portland vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Isle of Portland

Guest favourite

Bungalow in Dorset

4.94 out of 5 average rating, 49 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Aug. 30 – Sep. 6

$134 CAD per night

Condo in Dorset

4.85 out of 5 average rating, 53 reviews

Spacious and Modern Home

Feb. 4 – 11

$192 CAD per night

Guest favourite

Townhouse in Dorset

4.99 out of 5 average rating, 79 reviews

3 Storey, 4 bed town house, with street parking

Sep. 4 – 11

$210 CAD per night

Guest favourite

Townhouse in Dorset

4.96 out of 5 average rating, 95 reviews

Stylish Townhouse in Portland, Dorset

Sep. 2 – 9

$183 CAD per night

Guest favourite

Condo in Dorset

4.87 out of 5 average rating, 23 reviews

1 Bedroom Flat (Private Annex) with Parking

Jan. 27 – Feb. 3

$131 CAD per night

Guest favourite

Condo in Portland

4.94 out of 5 average rating, 70 reviews

Couples Luxury Retreat

Oct. 1 – 8

$183 CAD per night

Guest favourite

Home in Dorset

4.94 out of 5 average rating, 18 reviews

Our Place in Portland Cosy Cottage with a Sea View

Oct. 1 – 8

$220 CAD per night

Guest favourite

Guesthouse in Easton

4.96 out of 5 average rating, 71 reviews

Characterful 2-bedroom cozy cottage with garden

Aug. 26 – Sep. 2

$235 CAD per night

Destinations to explore