House holiday rentals in Weymouth and Portland District

Guests Favorite Coastal Cottage, walk to beach

Our cottage is on the southwest coastal path, a couple of minutes walk to the beach and sleeps 7. It's dog-friendly, free parking & ideally located to enjoy family holidays and watersports with safe beaches for swimming. Quiet tranquil area but near enough for each access to all the main attractions. Bedroom 3 can either be a king-size bed or set up as a twin with two single beds. It looks onto safe green areas for children & dogs to play. The cottage is well equipped. Saltpath_cottage

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.

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.

The Stable

The Stable is a stylish converted barn for two, or a couple with a young child, set on a peaceful working farm in Broadoak. Surrounded by rolling hills and country walks, it’s just a short drive to Bridport and the Jurassic Coast. The spacious interior blends comfort with character, and outside there’s a private, landscaped garden with lawn and patio — perfect for relaxing after a day exploring Dorset.

The Old Post Office - Weymouth Harbour Home

This is a 2 bedroom house with a very small front garden (no back garden) a few seconds away from Weymouth Harbour. We bought the house after staying in the one next door on holiday and loving the area and everything about Weymouth! There is an additional living room in the loft with a bar table, sofa and TV. We have a dog and will allow one well behaved dog and would prefer they stay downstairs.

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.

Cottage in Bower Hinton

Beautifully finished one bedroom barn conversion, part of Hillside Farm- a 19th Century hamstone barn. Carefully renovated with king size bed, generous walk in shower, open fire and well equiped kitchen to make your stay as comfortable as possible.