House holiday rentals in Weymouth and Portland District

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.

Family · Location · TV

Home from home

Enjoy a stylish experience at this centrally-located accommodation. Coming with a friend but don’t want to share bed, bed settee available, request when booking. Nature reserve within a minute walk, off main road but short walking distance to beach, shops, pubs and local buses. Off road parking for 1 car, small outside seating area to enjoy your morning cuppa or evening drinks. Self contained with own front door. Stair lift on request, bathroom has low level access shower, handrails and seat.

Family · Location · Walkability

Stone's Throw, Portland, on the Jurassic Coast

Stone's Throw is an open plan, modern house set in a residential development which was voted Supreme Winner of the Housing Design Awards. The development forms part of the 2012 Olympic legacy. Stone's Throw was home to the Trinidad and Bermuda Olympic sailing teams. The house is overlooking the green on Ben Ainslie Square and is a few minutes walk from Chesil Beach, Portland Castle, Marina, Sailing Academy, pubs and cafes. The Iconic Portland Bill lighthouse is a nearby visitor attraction.

Family · Location · Beach

Cottage 5 mins walk to Harbour

Your family will be close to everything when you stay at this centrally-located cottage. Coral Cottage is only 5 mins walk to the harbour & town and 10mins walk to Weymouth’s blue flag Sandy beach. Coral Cottage has been refurbished to a very high standard and as a former Victorian railway cottage it is full of character and is a perfect retreat for families or couples. It is ideally situated for the harbour, marina, beach, cafes and shops, with a nearby supermarket to hand.

Family · Location · Indoor spaces

Cosy Chesil Beach Getaway - Weymouth *no fees!*

Welcome to our beautiful static caravan, situated on the 5* award wining Chesil Beach Holiday Park. You can enjoy views across Chesil beach towards to the Isle of Portland. Ideal for making the most of all that Weymouth has to offer, as well as Portland and the Jurassic Coast. It is also perfectly located for walking the infamous South West Coast Path, which runs along the bottom end of the site. ** PLEASE NOTE, WE DON'T PROVIDE BED LINEN** One dog per booking welcome.

Location · Value · Sleep quality

Art-Filled 2-Bed, Suntrap Garden, 2 Min to Beach

An art-filled coastal home two minutes from Weymouth's beach, with a walled suntrap garden and hand-painted murals by my sister throughout. It's a house with a bit of soul — five years of slowly layering it with the things that actually matter: a deep bath for long soaks, soft bedding, fast Wi-Fi, proper wine glasses, and the small thoughtful touches that make a stay feel easy. A base for sea swims, coastal walks, Sunday roasts, or a slow weekend with nowhere to be.

Value · Family · Quiet

Spacious luxury home | 200m from beach | parking

Set on a quiet street close to everything, this renovated Victorian townhouse offers a calm, comfortable place to settle in and relax. Guests often mention how clean, stylish and genuinely homely it feels. With generous living space and thoughtful touches throughout, it suits both families and groups of friends. You’re just a short walk from the station, beach, harbour, shops, cafés and restaurants, making it an easy, well-equipped base for a laid-back coastal stay.

Location · Family · Indoor spaces

The Palms at No10 - Spacious and Family Friendly

Welcome to the Palms at No10! Unwind in this stylish and beautifully appointed home for your stay on the Jurassic Coast. The property offers ample space for 6 guests across three stunningly finished bedrooms, and our outdoor terrace provides al fresco to unwind after a day exploring everything Dorset has to offer. The Palms is perfectly located for a coastal getaway, with both the town centre just a short 20 minute walk away and the seaside only a stones throw away.

Family · Value · Laundry

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.

Value · Family · Beach

Weymouth house, full of plants and near the sea

welcome to our Airbnb, its light with modern decor and indoor plants a plenty. 10 min walk to Portland Harbour with easy access to the Rodwell Trail which connects it's location to town and Chesil/Portland by foot. Great location for water sport, nature and more. ** Please note this property isn't suitable for 5 adults**

Value · Location · Access

Character 4 bedroom house, Weymouth Harbour

Hartlebury End... your stunning home from home just a few minutes walk from Weymouth's outer harbour, town & beautiful sandy beach. Own car port & lovely enclosed garden. (I have 2 Airbnb's and the other one is on the harbourside, smaller and pet friendly so that will explain the reviews!)

Family · Location · TV

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 (size of parking space 3 x 5m). Located in the heart of the Jurassic coast, moments from Chesil Beach, local shops, pubs and cafes.

Family · Value · Check-in