Holiday houses in Winston

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Top-rated holiday rentals in Winston

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Guest favourite
A spacious outdoor deck is surrounded by greenery, featuring two Adirondack chairs and a round fire pit with a gentle flame. Potted plants add a touch of nature, while soft lighting illuminates the area, creating a cozy atmosphere for evening relaxation.
Treehouse in Richmond
5 out of 5 average rating, 119 reviews

The Pines Treehouse @ Treetops Hideouts

The Pines Treehouse is nestled underneath a huge oak tree sitting high above the running water of Sand Beck. Nature cocoons you and you can reach out and touch the trees, see wildlife all around you amongst the pines. With breathtaking views through the tress and across the valley you are completely private having no other accommodation on the site making this a truly unique and special experience. A great effort has gone into creating this space to allow you to simply relax and reset in nature.

Guest favourite
The living room features a log burner set against a stone wall, surrounded by a cozy setup. A green sofa and a pink cuddle sofa complement the space, with a rustic coffee table adorned with decorative items. Exposed wooden beams span the ceiling, enhancing the cottage feel.
Cottage in Gainford
4.96 out of 5 average rating, 290 reviews

The Old Dairy Cottage

A romantic one bedroom cottage converted from an old dairy dating back centuries offering guests 5* luxury, full of original features set in the Victorian village of Gainford. Including a private yard to the rear with wood fired hot tub, double ended roll top bath in the bedroom, with a four poster bed, fully equipped kitchen, log burner in the living room to give that real country cottage feel along with exposed beams Comes with WiFi, Netflix, alexa, spotify and a pub just a stones throw away

Top Guest favourite
A lodge made of dark wood stands beside a grassy area, with sheep grazing nearby. Rolling hills and trees are visible in the background under a partly cloudy sky. The fence leads to the entrance of the lodge, enhancing the farm's natural charm.
Cabin in Dacre
4.98 out of 5 average rating, 131 reviews

Forest View Lodge with hot tub and lovely views

Take a break and unwind at this peaceful farm stay in our lodge with electric hot tub and views of the forest and animals. The lodge is open plan with full kitchen, relaxing room with dining area and double bedroom, lots of clothing storage and bathroom with shower. We are situated on a network of footpaths through the Yorkshire Dales so a perfect walking retreat ending your days in the hot tub. We are a quiet location with several people living on the farm. Loud, drunk guests will be vacated.

Guest favourite
The entrance features elegant arched double doors framed by a natural stone facade. Light streams in through large arched windows, displaying a view of a cozy interior with a sofa and dining area visible beyond.
Cottage in Greta Bridge
4.96 out of 5 average rating, 140 reviews

Archer's Barn - Newly converted Oct 22 Sleeps 6

Brand new stone built cottage with beautiful arched windows, and countryside views situated between the towns of Barnard Castle and Richmond near Teesdale and The Yorkshire Dales. The property has close links to the A1 and A66 making a perfect location to explore the local area. High force, Hamsterley Forest, Eggleston Abbey are all within a short commute. Whilst local beaches, and the Lake District are within an hour's drive. The property sleeps up to 6 adults in 3 bedrooms and 2 bathrooms.

Guest favourite
The still waters of the River Tees reflect the surrounding greenery and blue sky. Lush trees line the riverbank, creating a serene atmosphere. The rocky shoreline features smooth pebbles, contrasting with the calm waters.
Apartment in Gainford
4.91 out of 5 average rating, 264 reviews

The Nook, a bright, modern and charming apartment

Centrally located in the fantastic village of Gainford which is set on the banks of the River Tees. The Nook is a beautifully appointed modern and bright two bedroom apartment, full of charm and character which overlooks the village. The apartment shares a Victorian building with its sister apartment, The Loft, and the Village shop. Opposite is the warm and friendly village pub, The Cross Keys, and 200 yards away is the village green with off road parking provided in the car park opposite.

Guest favourite
A charming entrance features a wooden bench set against a stone wall, surrounded by blooming greenery. Sunlight filters through the nearby window, highlighting the inviting door, which is partially shaded by an overhang.
Guest suite in Gainford
4.9 out of 5 average rating, 171 reviews

A quirky Cottage Studio in Gainford nr Teesdale

A recently renovated quirky Studio (sleeps 2) within the The Old Post Office, a Georgian stone built cottage in a quiet area tucked away on High Green in Gainford Village, 2 mins walk through the old Churchyard down to the River Tees. Popular with cyclists & walkers, the Market Towns of Barnard Castle & Darlington only 8 miles away, North Yorkshire Dales a 20 minute drive. Entrance accessible at all time via key safe. Hosts live on the property. No smoking 1 small dog allowed £35/sty

Top Guest favourite
A spacious bedroom features a large bed covered with a plush navy blanket. Two decorative pillows add color against the white bedding. Natural light enters through two skylights, enhancing the clean, modern design of the space.
Loft in North Yorkshire
4.99 out of 5 average rating, 240 reviews

Rural Retreat Loft bordering the Dales

Enjoy our cosy loft style apartment. Situated close to the historic market town of Richmond, nestled on the edge of Middleton Tyas Village is our loft apartment - suitable for couples, young families or friends looking to explore North Yorkshire and the North East. Sleeping upto 4 people (1 king bed/2 singles + 1 double sofa bed), this is the perfect country retreat for those looking for a romantic weekend away, a bit of privacy for a local wedding, or a base to explore the North.

Guest favourite
Cottage in Barnard Castle
4.94 out of 5 average rating, 110 reviews

Historic cottage beside the Tees, Yorkshire/Durham

A haven for walkers, swimmers and lovers of nature. With history and culture on the doorstep. Boot and Shoe is beautifully situated on the banks of the river Tees, 5 miles from Barnard Castle in the pretty hamlet of Wycliffe. Outdoors an abundance of wildlife, river swimming and tennis court; indoors cosy wood stoves and all mod cons. Ideal for visiting historic Raby Castle, Auckland Palace and Durham City and the wilds of upper Teesdale and the Yorkshire dales.

Top Guest favourite
A charming stone cottage is nestled among lush greenery, with a gravel pathway leading to the entrance. A luxury hot tub is positioned on a patio, surrounded by potted plants, while clear blue skies enhance the serene setting.
Cottage in Barningham
4.88 out of 5 average rating, 121 reviews

The Cottage at Wilson House

Delightful farm cottage amidst beautiful rolling countryside. Located beside owner's home but retaining an element of privacy. Private luxury spa hot tub for guests use with outside seating area and BBQ. Ample on site parking. Comfortably furnished throughout with full central heating & en-suite bathrooms. Located 10 miles from Richmond and 5 miles from Barnard Castle. Durham, York, Newcastle and the Lake District are approximately each an hours drive away.

Guest favourite
An outdoor patio area features a rectangular table with six black chairs, surrounded by gravel and greenery. A fire pit stands nearby, and a hot tub is visible at the far end of the yard. The scene is bright under clear blue skies.
Cottage in Winston
4.93 out of 5 average rating, 188 reviews

Luxury cottage with hot tub - Barnard Castle

Stables Cottage is a luxury and spacious rural holiday home just minutes' drive from the historic market town of Barnard Castle. Perfect for family holidays and relaxing romantic breaks. The idyllic luxury cottage has stylish interiors and a large hot tub. Included is a patio and garden with children's playground and activities. In addition, a plain jane bbq and firepit can be supplied on request. Please note ; small hot tub charge (see other)

Top Guest favourite
A graceful deer stands amidst tall grasses in an open field. The deer is adorned with a distinctive spotted coat and prominent antlers. Lush green hills and a fenced area are visible in the background, creating a serene rural setting.
Home in Austwick
4.97 out of 5 average rating, 155 reviews

Countryside Spacious Lodge with Unique Wildlife

A beautiful timber bungalow lodge set in a stunning location on the edge of a working farm. Within a conservation area & AONB its elevated position offers views of Ingleborough and Pen-y-ghent. This high quality Lodge offers extremely spacious accommodation, flexible sleeping options and is full equipt for your stay This is a perfect location for cycling and walking holidays with the Three Peaks and stocks reservoir within easy reach.

Top Guest favourite
A handcrafted cabin is framed by lush greenery, with natural wood siding that complements its surroundings. A wooden footbridge leads up to the entrance, where large glass doors invite light and offer views of the peaceful forest.
Cabin in Hawnby
4.97 out of 5 average rating, 137 reviews

Brook- Luxury, off grid, woodland cabin by stream

The Lazy T is the perfect sanctuary to switch off, find some solitude, read that book you’ve been wanting to open for a while, forage for food, immerse yourself nature, enjoy evenings of peace and quiet- the hooting of the owls, the crackle of the fire and the babbling brook. The Lazy T focuses on bringing us back to simple pleasures that, in the right place and company, become so deeply felt.

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