Holiday houses in Fortuneswell

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Top-rated holiday rentals in Fortuneswell

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Top Guest favourite
An open plan kitchen and living area is showcased, featuring a modern kitchen island with three high bar stools. The living space includes a comfortable sofa accented with several cushions, while large windows allow natural light to fill the room.
Condo in Portland
4.92 out of 5 average rating, 590 reviews

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach 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 showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

Guest favourite
A fire pit is positioned on a stylish outdoor table, with flames dancing under a colorful sunset. The horizon reveals the sea, while silhouettes of nearby rooftops and a wooden structure frame the scene.
Home in Portland
4.91 out of 5 average rating, 75 reviews

Sunset Cottage

Welcome to our beautiful cottage on the magical island of Portland. Relax on the terrace as the sun sets, fire up the pizza oven, curl up with a book by the warming log burner or enjoy a soak in the rolltop bath. Within very easy access to the sea and a wide selection of great, dog-friendly pubs and restaurants, Portland is perfect for active families or couples wanting to escape from all the hustle and bustle of life. Pet blankets are provided so you can snuggle up with your pooch on the sofa.

Guest favourite
A balcony with panoramic sea views is highlighted by a small dining set featuring four yellow chairs and a matching table. Sunlight illuminates the area, enhancing the inviting space for relaxation or meals.
Townhouse in Portland
4.91 out of 5 average rating, 141 reviews

Bright & beautiful 4 bedroom house with sea views

We're very excited to have installed a large balcony overlooking the sea, we hope you'll fall in love with Coastguard's Vantage as much as we have. Many of the rooms have sea views A 3min walk from Chesil Beach, it's the perfect base for experiencing the world famous walks We'll give you a guide about all the free parking spaces within 2mins walk from the house A utility room with washing machine & dryer has space to store boards, sails etc It's also close to the National Sailing Academy.

Superhost
A historic three-story stone house is framed by blooming flowers in the foreground. The structure features large windows and a welcoming entrance, set against a clear blue sky, showcasing its charm and inviting atmosphere.
Townhouse in Portland
4.86 out of 5 average rating, 169 reviews

Historic Seaman Chaplaincy, Seaview All Rooms

The Gift House Portland is a historic Seaman's Chaplaincy, 3 storey late Georgian stone house. All 4 spacious bedrooms have sea view & perfect for sunset watching. Dog friendly (1dog only) Locate in island village, 5-8 mins walk to pebble beach, 17th century pub, restaurants, good coffee, good chippy & grocery shop. Jurassic coast walks, sculpture park, Portland stone quarry, cycling, swimming, rock climbing, sea fishing, diving, kayak, sailing, paddling, windsurf & more are around.

Top Guest favourite
A cozy studio space features a double bed with textured bedding, complemented by soft blue cushions. A dining area with wooden seating is visible, along with a tall, narrow shelving unit and a television mounted on the wall. Warm, direct lighting illuminates the room.
Tiny home in Portland
4.85 out of 5 average rating, 85 reviews

The Studio - A seaside bolthole

The Studio is a cosy, tiny home with its own private parking, right outside. The garden, private access and facilities allow The Studio to stand out from the crowd and you to make the place your seaside home from home. You are just a ten minute stroll from Chesil Beach, with its breath-taking seascape, especially at sunset. With the stunning scenery and the multitude of activities, we feel sure that you will love your time spent in delightful Dorset and make lots of lasting memories.

Guest favourite
An expansive view of the sea captures the vibrant hues of sunset blending into the sky. The foreground features charming stone houses, while the calm ocean reflects the warm colors of twilight, creating a serene coastal scene.
Home in Portland
4.94 out of 5 average rating, 126 reviews

Charming Portland house with sea and sunset views

Welcome to our renovated Dorset getaway. Our Portland stone house is 5 minutes walk from Chesil Beach and 20 minutes walk to the Weymouth & Portland National Sailing Academy. The Isle of Portland is an idyllic spot to relax with stunning sea views or base yourself to explore the many activities in the area: walking, coasteering, horse riding, sailing, water sports, alpacas etc. The house is perfect for a self catering getaway but there are great restaurants a short walk away.

Top Guest favourite
The image captures a scenic view through three large windows, showcasing a vibrant sky with scattered clouds above the sea. The expansive blue water reflects the light, while distant coastal homes are visible in the foreground, contributing to a serene seaside ambiance.
Home in Portland
4.92 out of 5 average rating, 63 reviews

Beautiful cottage with sea views & sunsets

Beautifully presented period cottage with a ‘boutique’ feel, just a quick stroll from Chesil Beach. ‘Sergeants Retreat’ offers beautiful sea views & sunsets all year. Newly refurbished, Grade II listed police house provides flexible accommodation to sleep six and has easy parking. A sloped rear garden allows access to the sun and a chance for a barbecue or alfresco dining. Ideally positioned for walks, local pubs, cafes, shopping, day trips and sports or just to relax in by the sea.

Guest favourite
Apartment in Portland
4.8 out of 5 average rating, 183 reviews

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

Top Guest favourite
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 Portland
4.99 out of 5 average rating, 336 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.

Guest favourite
Townhouse in Portland
4.95 out of 5 average rating, 301 reviews

CLOUD 9 🦚 Homely & Happy 😊 Near the Beach 🌊🐟🌞

Welcome home, welcome to CLOUD9🌅 Vintage-modern velvet luxury in the historic heart of Fortuneswell on the Isle of Portland🌊 Fully renovated 2019-2022, & designed with love🧡 Living/dining room, kitchen, downstairs w/c, enclosed garden. Spacious shower room plus 3 themed bedrooms 🦚🌸 with light sea views⛵️ Chesil beach, co-op, fish & chips & pubs close-by🐟 😊 Super fast 100mb+ WiFi. Fully equipped kitchen. *If booking for 1-2, loft room will be locked.

Guest favourite
An aerial view of a contemporary property nestled within a coastal village, highlighting a long stretch of Chesil Beach in the background. The image captures the gentle curve of the beach, framed by various houses and rooftops under a clear blue sky.
Home in Portland
4.88 out of 5 average rating, 118 reviews

Chesil Beach Mews Cottage

Enjoy everything the Jurassic Coast has to offer, whatever the time of year. Situated literally a stone’s throw from the majestic Chesil Beach, this contemporary 3 bedroom, 2 bathroom property, with private parking, is perfect for exploring or relaxing. The property is set back from the main road within a modern private gated mews, so the only noise you will hear at night is the sound of the sea.

Guest favourite
An aerial view captures the coastline along Chesil Beach, where a series of charming, low-rise houses line the shore. The sun casts a golden glow over the beach and surrounding hills, while the calm sea gently curves towards the horizon.
Holiday home in Portland
4.9 out of 5 average rating, 102 reviews

Chesil Beach Mews House

Situated just a stone's throw from the wonderful Chesil Beach, this small but perfectly-formed, contemporary 3-bedroom, 2 bathroom property, with private parking, invites you to relax and enjoy being by the coast. The property is set back from the main road, so the only noise you will hear at night is the sound of the sea.

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