Vacation rentals in Fortuneswell

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.

Chesil Cove Holiday Cottage

A Grade II listed traditional characterful fisherman's cottage located adjacent to the iconic Chesil Cove on the isle of Portland, part of the Jurassic Coast. The cottage is small & cosy with two bedrooms, upstairs wetroom & modernised kitchen with solid wood breakfast bar. The wooden stairs are very steep & narrow so the property is not suitable for young children/those with mobility issues. An enclosed south-facing backyard is a suntrap for private sunbathing, drying swimming/diving gear etc.

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)

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.

Fisherman’s cottage on Chesil Beach

Stay in a charming Grade II listed fisherman’s cottage, just steps from Chesil Beach. This beautifully renovated home is 30m from Chesil Beach and opposite the Cove House Inn. Walk to the marina for sailing, go diving or paddleboarding off Chesil beach, or step straight onto the South West Coast Path for stunning coastal walks. Weymouth’s sandy beach, harbour and restaurants are just a short bus ride away, making this the perfect base for exploring Dorset’s Jurassic Coast.

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.

BillWatch Cottage

A holiday retreat right by the sea, at "worlds end" with dramatic, ever changing sea views, and a view of a lighthouse. A characterful, peaceful cottage by the sea is just what you're looking for to relax and unwind. There is so much wildlife and beauty to see here! You'll be spoilt with incredible uninterrupted sea views from our luxury garden room, and amazed in the morning when you're sat up in bed with a cup of coffee, watching ships and sailing yachts go by!

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.

The Penthouse (Small but mighty)

Enjoy a stylish experience at this centrally-located place on the Isle of Portland. So many places to visit and all within a stones throw away from our newly refurbished Penthouse. Guest access- just off the road down a private drive with one parking space directly outside. The space- One small but stylish room with a double bed and luxury bedding. Mini fridge and kettle. En-suite modern bathroom, towels included. Check-in from 16:00pm Check out before 10:00am

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.

Luxury Coastal Bolthole · Hot Tub · Beach Access

Walk past what looks like a garage and discover a stunning coastal bolthole all your own. Perfectly formed for two, with uninterrupted sea views, an open-plan living space opening onto a sun terrace, and your own private steps down to Castle Cove beach. Soak in the hot tub, fire up the BBQ, and watch the boats drift by. All towels, toiletries, and even beach kit provided. A romantic, characterful hideaway on the Dorset coast.

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.