Guesthouse holiday rentals in Weymouth and Portland District

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Top-rated Guesthouses in Weymouth and Portland District

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Top Guest favourite
A wooden cabin with large glass doors and windows is shown against a clear blue sky. The entrance is framed by a stone patio, and greenery is visible alongside the cabin, enhancing its natural setting.
Guesthouse in Dorset
4.88 out of 5 average rating, 209 reviews

Cosy garden cabin in the centre of Wareham

Quiet & cosy cabin with own bathroom within Wareham walls hosted by a Tibetan & English couple. A good place to explore the Jurassic coast & attractions such as Durdle Door, Lulworth Cove, Corfe Castle, Studland, Swanage, Arne Bird Sanctuary, Monkey World, Bovington Tank Museum & Wareham Forest. 5-minute walk to the picturesque quay & town centre which has pubs, restaurants, cafes, supermarkets, buses to tourist attractions & a cinema. 10-minute walk to station. Parking on available on drive.

Guest favourite
A compact accommodation features a spacious bed with a neatly arranged blanket and a two-seater sofa. A mini kitchen area includes a kettle and sink. Natural light streams through a large window, highlighting the wood flooring and soft-toned walls.
Guesthouse in Southhill
4.84 out of 5 average rating, 285 reviews

Bright & Snug annexe with Parking in Weymouth

Welcome to our one bedroom self contained private accommodation with parking space in Weymouth. Consisting of a double bed, two seater sofa ( NOT suitable to sleep) , mini kitchen unit with sink, kettle & toaster, fridge, smart TV, chest of drawers, shower room. Weymouth town Centre, train station and Weymouth’s popular beach is a 20 minute walk through the RSPB nature reserve, where you will see swans, ducks & plenty of bird species. Pub, pharmacy & shop is only a 5 min stroll down the road

Guest favourite
A covered hot tub is featured in the foreground, with bubbling water inviting relaxation. In the background, a spacious garden is visible, showcasing a patio dining set shaded by an umbrella, a barbecue grill, and comfortable seating areas surrounded by greenery.
Guesthouse in Moreton
4.92 out of 5 average rating, 208 reviews

Full use: hot tub/sauna/bbq/firepit/Netflix/Prime

Little Oakford is your peaceful haven 'Far from the Madding Crowd' in the heart of idyllic, rural Dorset! At the end of a lane and on the edge of woods, from where birdsong can always be heard and in which deer can often be seen, its large private garden & all its amenities, including covered hot tub, gazebo, fire pit & 5 (s)eating areas, are for your free & exclusive enjoyment. With its free parking, kitchen, steam shower, superfast WiFi, 4K TV & Netflix, it's perfect for business or pleasure.

Guest favourite
A modern outdoor decking area is shown, featuring a dining set with four chairs around a glass-topped table. Lush green plants are visible, and the sunny sky is partially filled with fluffy clouds, creating a serene setting for relaxation or al fresco dining.
Guesthouse in Dorset
4.96 out of 5 average rating, 136 reviews

Palm Cottage

A good sized modern One bedroom garden annex only a short walking distance to local pub, take away, convenience store & hairdressers with a 20 minute walk into the Town Centre and Beach (£6 - £7 taxi ride) Weymouth is a very popular tourist attraction with numerous high end eating establishments, a superb beach and harbour which are particularly vibrant during the Spring and Summer months, a golf course and a railway station. Only 13 miles from the picturesque Lulworth Cove & Durdle Door

Superhost
A spacious sleeping area features a large tufted headboard in a blue hue. Soft lighting is provided by a pendant lamp, while patterned wallpaper adds texture. Two decorative pillows rest on the bed, and natural light filters in through the window covered by dark curtains.
Guesthouse in Dorset
4.94 out of 5 average rating, 267 reviews

Seaside studio cabin minutes from 'secret' beach

Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

Top Guest favourite
A charming exterior view of a light blue cottage with a dark roof and two front doors. Neatly trimmed bushes line the pathway, and a small outdoor area is visible. The structure is surrounded by greenery, with a clear blue sky overhead.
Guesthouse in Piddlehinton
4.97 out of 5 average rating, 209 reviews

The Yorkshireman @ Piddlehinton

We are so excited about our conversion. Completely self-contained, it is a lovely, light, cosy open space with a well equipped kitchen, modern bathroom and a cool sleeping platform/mezzanine. Piddlehinton is a special place, 20 mins from the Jurassic Coast and 10 mins from Dorchester, in the renowned Piddle Valley, with beautiful walks, views and our award winning pub, The Thimble Inn. We are right next door if you need anything, but if you prefer your privacy, you can be totally separate.

Guest favourite
A comfortable sleeping area is highlighted by a spacious bed adorned with patterned pillows. A wall-mounted TV and a small desk with a chair are positioned nearby, alongside a stylish shelving unit that adds functionality and aesthetic appeal.
Guesthouse in Dorset
4.96 out of 5 average rating, 581 reviews

The Cabin - Hot tub vibes

**Building work next door June to September** price reduced by 25% to reflect this and anyone staying will need to accept there may be some noise pollution. This is a space for people who want to relax or explore the amazing area of Dorset. Sandbanks beach - 10 min drive. Durdle Door - 30 min drive. Studland - short ferry ride from Sandbanks We have a driveway so there is parking available for you if you travel by car. We also live a 5 - 10 minute walk from Poole town centre. No pet

Guest favourite
The spacious living area features a comfortable seating arrangement with a coffee table and a dining space. Natural light floods in through large glass doors, which open to a private garden view. A cozy bed is situated against a light-colored wall, complemented by decorative accents.
Guesthouse in Dorset
4.95 out of 5 average rating, 483 reviews

Beautiful Cosy Retreat & Hot tub, near beach

Although the Annexe is part of our family home, we no longer live in the house & the property is only for guests staying at the annexe. During your stay explore the Dorset coast & forests, eat delicious meals at our local restaurants & pubs, spend a relaxing evening in fully covered hot tub surrounded by festoons lights, or spend the afternoon in the garden. The Annexe is a couple minutes walk away from pubs, restaurants, M&S & Tesco & lovely woodland walks. Sky sports is include.

Guest favourite
The exterior of a wooden barn conversion features a spacious deck surrounded by a grassy area and colorful flower beds. Large windows provide a view into the interior, while the roof is covered with green tiles. A shaded area is located to the right of the building.
Guesthouse in Dorset
4.88 out of 5 average rating, 344 reviews

The Barn Little Birch

Wooden barn conversion that's been converted to the highest spec, on the edge of a pretty rural Dorset village. Only a few miles from the stunning Lulworth Cove and Durdle Door, there is plenty of walks attractions for all the family. The world famous Monkey world and Tank Museum is only a 10 minute drive away, you could also visit the ruins of Corfe castle with beautiful village it is set in. We are 20 minute drive from Dorchester which was the home of Thomas Hardy.

Guest favourite
A wooden guesthouse is nestled within a paddock, surrounded by tall trees. A well-maintained railing borders the property, and a small deck extends from the front. The exterior showcases a blend of rustic charm and modern design under a clear blue sky.
Guesthouse in Maiden Newton
4.88 out of 5 average rating, 122 reviews

A charming one bedroom guesthouse nr Maiden Newton

The Woodshed is a self contained guesthouse that is situated in a paddock behind our main house and in the heart of the glorious Dorset countryside, perfect for holidays and short breaks. A lovely one double bedroom property with secure private parking and a decking area with outdoor seating and stunning views of the Frome valley. Surrounded by rolling hills and close to some of Dorset's most treasured landmarks, this is a place to truly escape and relax. *NO PETS

Top Guest favourite
A dining area is seen with a neatly set table adorned with a floral tablecloth. Fresh tulips are placed in a vase, alongside breakfast items. Large windows open to the outside, providing natural light and views of the green landscape beyond.
Guesthouse in Lyme Regis
4.96 out of 5 average rating, 210 reviews

Cosy lodge, parking, beautiful setting, Lyme Regis

Relax with the whole family at this peaceful place to stay. One of two properties available, Beech Lodge is situated in a quiet spot with lovely views towards the Devon countryside. It is a five minute drive to Lyme Regis and is near a footpath that takes you via Uplyme along the River Lim for a meandering walk into Lyme's centre. It is an ideal base for exploring all that Devon and Dorset has to offer. Please read our reviews. Guests love staying here.

Guest favourite
The exterior of Lavender Cottage features a charming stone facade and a tiled roof. A white table with matching chairs is positioned outside, surrounded by vibrant flowers and greenery. The inviting outdoor area provides a setting for relaxation and enjoyment of the picturesque surroundings.
Guesthouse in Mosterton
4.96 out of 5 average rating, 113 reviews

Lavender Cottage, Mosterton, Beaminster, Dorset.

Lavender Cottage is a quaint little stone cottage situated in the grounds of 300 year old Sandiford Farm. With spectacular views of the Dorset countryside and decorated with french flair it's not only a walkers paradise but also just 20 mins drive from the Jurassic Coastline. If you're looking for a base to unwind and explore with a popular pub on your doorstep offering great food and drinks then look no further, this is the place for you.

Popular amenities for Weymouth and Portland District guesthouses

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