Holiday rentals in Winston

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.

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

Honeysuckle Shepherd’s Hut w/ Hot Tub and T/court

Off Grid shepherd’s hut with a wood fired hot tub and tennis court in the picturesque village of Potto, near Swainby. The perfect weekend getaway for 2 with stunning views of the North Yorks moors and a wood burner. This hut is cosy, warm and comfortable. The shepherd’s hut has a hot shower, working gas stove and a mini fridge. There’s a separate private composting loo. And during the summer you may use the tennis court just a short walk through the orchard. There is no electricity in the hut.

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.

Spacious 2 bed detached cottage, nr Barnard Castle

Haven Cottage is a self contained detached 2 bed stone cottage in rural Cotherstone near Barnard Castle. You have exclusive use. Set on a quiet lane, the converted stable overlooks open meadows. Outside is a patio garden & furniture. Enter via a double height dining hall, to an open plan kitchen and living room, traditionally furnished with exposed beams and deep window recesses. Downstairs is a large bathroom (bath & walk in power shower). Upstairs two large bedrooms with reading chairs.

The Loft, 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 Loft 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 Nook, 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.

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

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.

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.

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.

Luxury contemporary lodge with hot tub -

The lodge is extremely cosy with impressive countryside views. Hot tub and other extras can be added onto booking (see additional notes) It has a fully equipped kitchen and open plan living space that opens onto private decking with wood fired hot tub, outdoor shower (summer months only July and August) , al fresco dining, BBQ and firepit. There is an extremely large comfy king bed on the mezzanine with en-suite /shower.

Glamping Pod w/ BBQ Area & Onsite Café

🌿 Escape to Luxury on the Edge of the Durham Dales Wake up to fresh countryside air and your own beautifully crafted glamping pod. Set on the doorstep of the Durham Dales, enjoy peaceful views, modern comfort, and our on-site café serving breakfast, lunch, and homebaked cakes. Perfect for romantic escapes, family adventures, trips with friends or team retreats — it’s the ideal place to switch off and reconnect.