Holiday rentals in Winterborne Kingston

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Top-rated holiday rentals in Winterborne Kingston

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Top guest favourite
Barn in Dinton
5 out of 5 average rating, 159 reviews

Unique, romantic luxury countryside retreat

Unique luxury cottage for two, an ancient dovecote with a fabulous swimming pool. Beautifully furnished, romantic and spacious, in gorgeous peaceful countryside, the thick stone walls make it warm and cosy in winter, cool in summer as well as quiet and private. Upstairs there is a very comfortable super kingsize bed, a rolltop bath, a huge velvet sofa and a 50" TV. Downstairs is a shower room, kitchen and large dining area. Lovely walks from the door and close to Salisbury, Longleat & Stonehenge

Top guest favourite
A cozy sitting area features a plush olive green velvet sofa adorned with patterned and solid cushions. A stylish wooden chair complements the vintage aesthetic, while large artworks decorate the walls. Exposed wooden beams add character, and a patterned rug enhances the inviting ambiance.
Barn in Dorset
5 out of 5 average rating, 113 reviews

Artist’s Creative Hideaway & Sauna

Beautiful, inspiring, and peaceful, Arthouse is a place to escape. This converted art studio in West Dorset is close to Chesil Beach and the Jurassic Coast. It is surrounded by wildflowers and features contemporary art and sculptures by artists Rouwen and Reeve. The space is complemented by mid-century modern furnishings, high ceilings, and exposed beams. All doors open to a private patio and a naturalistic garden. The Sauna, located in the gravel garden looks out onto sculptures and plants.

Guest favourite
A spacious bedroom includes a comfortable bed with crisp linens and decorative pillows. Natural light brightens the room, enhancing the elegant slipper bath and the stylish chair nearby. Framed artwork adorns the walls, contributing to a serene ambiance.
Bungalow in Charlton Marshall
4.88 out of 5 average rating, 355 reviews

Ranmoor Estate - Hunters Cottage - Hot Tub & A/C

Welcome to Hunters Cottage – our most opulent luxury cottage at Ranmoor Estate, where refined comfort meets timeless countryside charm. This stunning, air-conditioned retreat is perfect for couples seeking a romantic escape. The main bedroom features a king-size bed and a beautiful slipper bath, creating the ultimate space to unwind. Outside, enjoy your private hot tub and BBQ area overlooking the rolling Dorset countryside — the perfect setting for relaxation, romance, and lasting memories.

Guest favourite
The exterior of the Victorian Reading Room is presented, showcasing a charming brick facade with light moss present on the roof. A welcoming entry door, framed by two chimneys, is complemented by modern windows. A vintage-style post box is positioned beside the entrance.
Tiny home in West Stafford
4.92 out of 5 average rating, 276 reviews

The Old Reading Room West Stafford

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

Top guest favourite
The blue Shepherd’s Hut is positioned on a grassy area, showcasing its charming curved design. Wooden steps lead to the entrance, inviting guests inside. Surrounding trees and a scenic countryside view enhance the peaceful setting.
Shepherd’s hut in Dorset
5 out of 5 average rating, 359 reviews

Luxurious Shepherd’s Hut with Hot Tub

Get back in touch with nature at this luxury Shepherd’s Hut nestled in a quiet hamlet. Enjoy the large hut’s interior amid thoughtful industrial style decor and modern finishes and embrace outdoor living in your own large outdoor space, surrounded by breathtaking views of the countryside. Relax in the large fire fuelled hot tub, lounge on the deck in front of the fire pit or grab a bean bag and find a quiet spot in your own private paddock. This place offers luxurious comfort indoors and out.

Superhost
A cozy living room is furnished with a spacious sectional sofa facing a wall-mounted TV. Large glass doors offer sweeping views of the sky and surrounding area. Green plants add a natural touch, while a sleek wood-burning stove creates a focal point in the inviting space.
Apartment in Westbourne
4.85 out of 5 average rating, 180 reviews

The Beach Hytte - Stunning Sea View Penthouse

Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Top guest favourite
The main living area features a spiral staircase leading to an upper level and an open-plan kitchen with a large island and breakfast bar. Natural light enters through large windows and bifold doors, enhancing the space that includes comfortable seating and greenery.
Home in Tarrant Gunville
4.99 out of 5 average rating, 151 reviews

Stylish Barn Conversion

The Barn is a converted property located at the head of the stunning Tarrant valley within the Cranborne Chase Area of Outstanding Natural Beauty. The main living area has dual aspect and bifold doors out onto an enclosed patio, garden and seating area. Two of the bedrooms have internal balconies into the main body of the barn and triple velux roof windows to enjoy the rural views. The third bedroom has bifold doors onto the patio and an en-suite with rainfall snail shower. TV/cinema room.

Top guest favourite
A charming brick and flint cottage stands under a clear blue sky. Symmetrical gabled roofs and evenly spaced windows enhance its facade. Lush greenery from nearby plants adds to the welcoming approach. A pathway leads to a wooden front door, inviting guests into a serene retreat.
Home in Hanford
4.99 out of 5 average rating, 135 reviews

Hanford Minima

Immaculate newly renovated three-bedroom cottage, (1 super king en suite, 1 king and 1 twin sharing a family bathroom) dating from the 1840s in typical Dorset brick and flint. Nestled at the foot of Hambledon Hill – between Shaftesbury and Blandford – it's only a mile to the excellent village shop and an easy walk over Hambledon hill to The Cricketer's pub for lunch or a pint. Drive to the Jurassic coast (40 mins) to explore Lulworth Cove or visit the gorgeous beach at Studland or Weymouth

Top guest favourite
A charming Georgian house presents a whitewashed façade, featuring large windows and a wide blue front door. The building is flanked by brick walls and mature greenery, creating a welcoming entrance on a quiet lane.
Townhouse in Blandford Forum
4.97 out of 5 average rating, 167 reviews

Old Red Lion House in Market Town

A beautiful listed building located on a quiet lane in the centre of the pretty market town of Blandford Forum, offering the perfect place to explore Dorset or simply relax in one of the cosy sitting rooms and indulge in one of the house's many books. Plenty of board games and DVDs will keep the younger ones entertained or get outside to the nearby River Stour to spot otters and kingfishers (just a 5 minute walk from the house) or head in any direction to Dorset's spectacular countryside.

Top guest favourite
An open living area features a modern, plush sectional sofa facing a large glass wall that connects to the outdoor space. Two small, round tables, one with a decorative tray, are positioned in front. Natural light fills the room, highlighting the simple decor.
Bungalow in Somerset
4.99 out of 5 average rating, 271 reviews

Modern & spacious house in the countryside.

The Pavilion is a modern, purpose built holiday house in the quiet Somerset village of Yarlington. It has all the conveniences: Wood burning stove, underfloor heating, Washer & tumble dryer, Iron & ironing board, fast fibre optic broadband and a charging station for an electric or plug in hybrid car, but sadly the mobile phone signal is very poor. The house is next to the pub and a stones throw from the church. The Newt and Hauser Wirth Gallery in Bruton are within a 15 minute drive.

Top guest favourite
The living area features a light, open space with a soft gray sofa and armchair, complemented by a round mirror and natural light from skylights. A dining table is positioned by a window, with a small ottoman placed nearby, all set on a neutral-toned rug.
Bungalow in Pimperne
4.97 out of 5 average rating, 148 reviews

The Covey - 1 Bedroom Annex with Country Views

Situated in beautiful Wessex this self-contained annex located on the outskirts of Blandford is within walking distance of amenities but retains a countryside feel overlooking fields. With one bedroom and separate living area it’s perfect for singles or couples A walk thru video of the property is available on YouTube on searching for TheCoveyBlandford Nearest pub - 10 mins walk Driving mins Nearest shop - Lidl 3 Blandford centre - 5 Poole & Bournemouth / beaches 30-40 Purbecks -40

Top guest favourite
A private garden features a round table surrounded by four chairs, set on a stone patio. Lush greenery and flowering plants border a well-maintained lawn, while a rustic shed is visible in the background under a clear blue sky dotted with clouds.
Cottage in West Knighton
4.94 out of 5 average rating, 304 reviews

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.

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