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, 535 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

Top Guest favourite
A cozy sitting area features a plush olive green velvet sofa adorned with patterned and solid cushions. A stylish wooden chair complements the vintage aesthetic, while large artworks decorate the walls. Exposed wooden beams add character, and a patterned rug enhances the inviting ambiance.
Barn in Dorset
5 out of 5 average rating, 112 reviews

Artist’s Creative Hideaway & Sauna

Beautiful, inspiring, and peaceful, Arthouse is a place to escape. This converted art studio in West Dorset is close to Chesil Beach and the Jurassic Coast. It is surrounded by wildflowers and features contemporary art and sculptures by artists Rouwen and Reeve. The space is complemented by mid-century modern furnishings, high ceilings, and exposed beams. All doors open to a private patio and a naturalistic garden. The Sauna, located in the gravel garden looks out onto sculptures and plants.

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, 126 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 vibrant blue door marked with the number '107' is featured prominently. The door is surrounded by textured Portland stone, highlighting the characteristic architecture of the cottage. A brass doorknob adds a classic touch to this welcoming entrance.
Cottage in Portland
4.86 out of 5 average rating, 177 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.

Top 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
4.95 out of 5 average rating, 111 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
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, 306 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.

Top Guest favourite
The entrance features a solid wooden door framed by two decorative lion statues, each placed on stone bases. Ambient lighting highlights the textured walls, and the home’s address can be seen above the door.
Holiday home in Portland
4.94 out of 5 average rating, 207 reviews

Quirky 2 bed holiday home with hot tub and sauna.

Newly built 2 bedroom cottage with hot tub and sauna located in Easton on Portland in Dorset. This unique home is built in Portland stone and has a ground floor outdoor space with patio and outdoor oven area as well as having an upstairs outdoor mezzanine area with bi-folding doors. The main living space that includes a 90” television. All equipped with sky Q including sports. Both bedrooms have super king beds and are en-suite with showers and jacuzzi baths.

Guest favourite
A living area features light-colored furniture, including a cozy sofa adorned with decorative pillows. A flat-screen television sits on a dark wooden unit. Artwork depicting a sailboat and a wooden oar add character to the walls. Natural light enters through a window with light shades.
Home in Portland
4.86 out of 5 average rating, 172 reviews

Fair Winds House

Fair Winds offers a getaway just a stone's throw from the ocean and Portland Marina with allocated parking and enclosed garden. Wake up to sea views 2 minutes walk from Portland Castle Beach, or 5 minutes to the renowned Chesil Beach. We have a brilliant bakery and the beachside sauna, both just around the corner. For a peaceful retreat or an adventure by the sea, Fair Winds is an ideal base for exploring the wonders of Dorset's stunning coastline.

Guest favourite
Townhouse in Portland
4.94 out of 5 average rating, 250 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 & designed with love🧡 Living/dining room, kitchen, downstairs w/c, enclosed garden. Spacious shower room plus 3 themed bedrooms 🦚🌸 with 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
4.89 out of 5 average rating, 101 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.

Top Guest favourite
Three sculptural wall hangings are showcased, featuring expressive faces partially obscured by hands. The textured materials create a striking visual contrast against the plain wall. Each piece offers a unique interpretation of emotion, enhancing the room's artistic ambiance.
Bungalow in Portland
4.94 out of 5 average rating, 174 reviews

Islands Wrest (The Cavern). Twin/Dbl Rm. Pets ok.

Cavern themed room with own entrance, kitchen & shower room. This is your own space within owner occupied property. Zip link bed, room can be twin room (2 x single beds) or double (king sized) bed. I have another adjoining accommodation that is slightly bigger with an added conservatory. There may be other guests using this space. Not suitable for infants (Adults only)

Guest favourite
A living room area features a cozy beige sofa adorned with grey and purple cushions. A framed mirror and artwork decorate the wall above a white mantel, where a log burner emits warmth. A woven basket and lamp provide additional lighting in this inviting space.
Cottage in Portland
4.86 out of 5 average rating, 451 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.

Popular amenities for Fortuneswell holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Dorset
  5. Fortuneswell