Vacation rentals in Fortuneswell

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Top-rated vacation rentals in Fortuneswell

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Guest favorite
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, 74 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 favorite
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 mid 1800s stone cottage sits on a sloping street, featuring a red door that contrasts with the gray exterior. The distant sea is visible beyond neighboring rooftops, under a sky with scattered clouds. The scene captures the unique hillside setting of the property.
Home in Portland
4.87 out of 5 average rating, 61 reviews

Cove Cottage: minutes to sea, and sunset views

This unique mid 1800s Grade II listed Portland stone cottage is just three minutes away from Chesil beach, and the famous beachside Cove House Inn. With stunning sunset views from the garden, it is also within a stone’s throw of Portland marina and all its watersports and close to renowned restaurant The Crabhouse Cafe. Minutes away is a bus stop that will take you to Weymouth with its famous sandy beach and picturesque harbour. Or venture up the hill to Church Ope Cove and Portland Bill.

Top guest favorite
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, 84 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 favorite
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 favorite
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
4.93 out of 5 average rating, 61 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.

Top guest favorite
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 favorite
Townhouse in Portland
4.95 out of 5 average rating, 300 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 favorite
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, 117 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.

Superhost
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.
Vacation 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.

Guest favorite
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
4.87 out of 5 average rating, 470 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.

Guest favorite
A wooden chalet features a charming entrance with double French doors and a small window, both framed by natural wood finishes. A welcome mat is positioned at the threshold, and a concrete path leads to the door. The surrounding area includes green plants and a quiet, rustic ambiance.
Guesthouse in Portland
4.71 out of 5 average rating, 246 reviews

Self-catering Chalet with Parking

Kitchen area with electric hob, combi-microwave, kettle, fridge, toaster and basic equipment for self-catering. Shower room. Dining area Living area has sofa bed and chair bed+ bunk beds. Bed linen and towels provided. TV / DVD player Covered Drying Area Parking This a non-smoking property including the garden area.

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