Cottage holiday rentals in Weymouth and Portland District

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.

Romantic hillside hideaway with outstanding views

A unique and romantic hideaway, Quarryman's Cottage is dinner on the roof terrace watching the sunset over Lyme Bay & Charmouth, stargazing from the luxury freestanding bath, epic views from the double shower, reading under the old oak tree, BBQ's & firepits, leisurely walks to The Anchor at Seatown via Golden Cap or the coastal path, the sound of birdsong, the glimpse of a deer, curling up in front of the wood burner in winter. It is a tranquil & heavenly escape from the bustle of daily life.

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Cottage close to Beach & Old Harbour with Parking

Sydenham Cottage | Stylish Coastal Retreat with Parking | Walk to Beach & Harbour Beautifully refurbished to a high standard, Sydenham Cottage is a stylish and comfortable base for your Weymouth stay. Just a 2-minute walk from the bustling harbour and moments from the award-winning beach, it’s perfect for exploring cafés, restaurants, and the coast. Prices shown include Airbnb’s 18.6% booking fee. This property is also available to book on other platforms, where prices and fees may differ.

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

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.

Cobb Cottage - Harbourside, permit parking

Cobb Cottage is a stylish hideaway, tucked down a cobbled side street in the heart of Weymouth's historic harbour. The cottage has been lovingly converted from a former bookshop into a contemporary, centrally located holiday home with easy access to Weymouth harbour. Perfectly suited for two couples or a family, with three bedrooms and two bathrooms. There is a parking permit to for one car which provides free parking on street outside the cottage, or in a nearby car park. Dog friendly!

Jasmine Cottage

Jasmine Cottage is a characterful, compact barn conversion, that sits next to the 400 year old farm house. It sleeps up to four people (including infants), with a double and a twin room. We are one mile away from The Wise Man Inn - an award-winning pub; 6 miles from Dorset's stunning Jurassic coast and 3 miles from the county town of Dorchester. You will, however, need a car- or bikes! Sorry, no pets and no smoking. No EV charging, yet, but there are many fast charging points nearby.

Cove Garden Cottage with enclosed sea view garden

Magical sunsets and magnificent coastal walks. Stop the clock relax and enjoy all that this little haven on the Jurassic coast has to offer. Something for everyone from chilling and reading to water sports such as sailing, kite surfing and paddle boarding. There are plenty of local pubs, restaurants and cafes to choose from too. Some of the best in walking distance. The local art and music scene is very established. This is a great spot to explore the Dorset coast and venture inland.

Harbour's Edge Cottage - Nothe Parade, Weymouth

Beautiful harbourside cottage with fantastic outlook onto Weymouth harbour. This two bedroom cottage is delightfully decorated and has everything you need for a wonderful vacation. The kitchen is really well equipped & there is a washer dryer. The dining area (ground floor) is great for an evening meal & there is a view of the harbour from many of the rooms. The lounge has amazing views of the harbour and is located on the first floor along with the twin bedroom and main bathroom.

A Charming Cottage, Just a Moment from the Beach

Right on the gateway of the best beach in the United Kingdom. This is an excellent place to get your Weymouth adventure underway. Sympathetically updated and located a moment from the beach and train station; it'll suit most visitors needs. We've tried to update the cottage in keeping with a turn of the century victorian home, yet keeping it stylish and up to date with all the mod-cons you would expect. We're located close-by, so we're on-hand to support your trip. Enjoy.

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.