Holiday rentals in Isle of Portland

1888 Portland stone cottage

1888 Portland stone cottage, with many original features. Stone fireplace with log burner. Cosy 2 bedroom, 3 storey cottage located within easy walking distance of Easton Square, which has local amenities, including grocery stores, chemist, pubs and cafes. Small sunny aspect courtyard with bistro table and chairs. A perfect holiday location all year round, for either sun and relaxation, or enjoy activities like windsurfing, sailing, diving, rock climbing, fishing, walking and bird watching.

Blue Skies Retreat,Modern house Chesil Beach

Modern semi-detached house located two minutes walk from Portland Marina and Chesil beach. Perfectly situated for divers, walkers sailors and anyone who pursues water based activities. Pubs restaurants and takeaways within walking distance of the house. Private parking situated at the front of the property. This house has a modern contemporary interior with two double bedrooms. One of these with twin beds. Enclosed rear garden with patio and seating area perfect for watching the Chesil sunset.

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.

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)

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

Coast - White Stones Studios

Come and enjoy our new and unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

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

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

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” smart television. Both bedrooms have super king beds and are en-suite with doors to outside access and large smart tv screens