Holiday houses in Fortuneswell

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Fortuneswell

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
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, 546 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, 117 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.

Top Guest favourite
A round porthole window features a serene view of calm waters reflecting the sky. A distant rocky shoreline with palm trees can be seen on the left side, framed by a textured wooden wall.
Bungalow in Portland
4.95 out of 5 average rating, 222 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this your own space within owner occupied property. Explore Portland, an Island that features breathtaking views, beautiful walks. Castles, 3 lighthouses. Chesil beach. a Museum, rock climbing, wildlife, water sports. History of smugglers & pirates explore Church Ope Cove. 20 min on bus to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem. Not suitable for infants (Adults only)

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, 131 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.

Top Guest favourite
A modern three-story house features natural stone cladding and large windows. The entrance is framed by a neatly landscaped front garden with shrubs. A path leads to the front doors, showcasing the welcoming façade of the property within a quiet development.
Townhouse in Portland
4.98 out of 5 average rating, 115 reviews

Modern & spacious 'Olympic' House by the sea

A stylish, 3-storey 'Olympic' house on the beautiful Isle of Portland, Dorset. Moments from the beach, this modern 3 bedroom house comfortably sleeps 7 (+2 available on request) A large open-plan kitchen, dining & living space adjoins a private, enclosed garden that is a real sun-trap. Chesil Beach, WPNSA (National Sailing Academy), great pubs & restaurants, a park, skate park, sculpture park & the coast path are all on your doorstep. It is the perfect base for exploring the Jurassic coast.

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, 112 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.

Guest favourite
Gentle waves lap against smooth rocks along the shoreline, reflecting soft hues of pink and blue in the evening sky. The rugged cliffs outline the horizon, creating a serene natural landscape that evokes the tranquility of the coastal environment.
Home in Portland
4.77 out of 5 average rating, 136 reviews

Portland Stone Cottage on Chesil Beach

Three storey house with a recently refurbished kitchen. Neutral decor, plenty of space for a large family, outdoor patio with seating area, two TVs, central heating throughout, fridge/freezer, washing machine, bathroom with bath/shower, separate toilet. 1st floor: Double bedroom with TV and a single bedroom . 2nd floor: large bedroom with a double and single bed. A stone's throw away from Chesil beach, supermarket nearby, on the bus route, sea views and a peaceful neighbourhood.

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, 313 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
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
4.85 out of 5 average rating, 178 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.

Top Guest favourite
Townhouse in Portland
4.95 out of 5 average rating, 264 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, 104 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
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, 456 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