House holiday rentals in Weymouth and Portland District

Seaside Retreat – Cosy 2-Bed, Garden & Murals

Welcome to your seaside escape — a cosy, art-filled hideaway just two minutes from the beach. This relaxed little home is full of personality, plants, and sunshine. My sister’s hand-painted murals and original artwork give the space a creative, soulful feel, and the private garden (a total suntrap in summer) is perfect for morning coffee or evening drinks. Whether you're here for sea swims, a weekend reset, or just a change of pace, this is the kind of place made for feeling at home.

Woodpeckers Rest - Alpacas-Gardens-Brook-Tennis

Nestled in an area of Outstanding Natural Beauty, Wynford Eagle is one of West Dorset's hidden gems. Woodpeckers Rest is a cosy studio retreat, a haven for peace and relaxation which opens out onto a large terrace with stunning views of the valley, 8 acres of grounds and gardens and beautiful alpacas. A great base to explore Dorset, situated just 15 minutes from the Jurassic coastline and all this incredible area has to offer. Please also see listing for airbnb.com/h/swallows-return

Chesil Cove, Portland's jewel

Detached house in beautiful Chesil Cove, literally a pebble's throw from the sea. Perfectly situated for divers, sailors, walkers and anyone who enjoys beach life. Private parking for 2/3 cars. Pubs, restaurants and takeaways all in easy walking distance. Special features for divers and watersport fans include a hot water outside shower, lockable shed for stowing gear and drying racks for wetsuits. Well behaved dogs welcome. Dog towels and a cosy alcove for their bed available.

Olly's Retreat

Step inside Olly's and you'll be impressed by the modern and stylish interior and the benefit of a sunny private courtyard. Accommodation consists of a large open plan modern living space, with integrated kitchen. The large bathroom with power shower is also located on the ground floor. Upstairs two generous bedrooms, one with a king size bed and the other twin beds. The property sleeps four and we also accept dogs (however please do not leave them alone in the property)

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.

Cheerful one bedroom home in the heart of Dorset

A great base for exploring Dorset and centrally-located. This newly decorated self contained 1 bedroom annexe has a fully equipped kitchen & in the county town of Dorchester, the birth place of Thomas Hardy. It is a perfect base to explore the beautiful countryside and Jurassic coast! The town’s amenities are only a short walk away including the new Brewery Square development. Complimentary tea and coffee also provided.

Luxurious hideaway near Lyme Regis

Little Staddles is a contemporary cedar clad chalet, set in a pretty woodland, in an Area of Outstanding Natural Beauty, just a couple of miles from Lyme Regis. With a super king sized cosy bed, woodburner, luxurious bathroom, outdoor hot tub and heated outside shower... it really is the perfect place to relax and unwind.

Beautiful spacious home & garden

Kick back and relax in this calm, stylish space with a beautiful garden and wildlife pond. 15 mins walk from Weymouth’s award winning beach and Lodmoor Country Park (seasonal miniature steam train, Sealife Centre and Sandworld). Easy reach of Weymouth’s historic harbour.

April's Cottage, sea views close to Chesil Beach

Escape from it all in this little cosy character cottage crammed with history and home comforts including own parking right outside your front door. Located in the heart of the Jurassic coast, moments from Chesil Beach, local shops, pubs and cafes.