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Holiday rentals in Winston

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Top-rated holiday rentals in Winston

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 105 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.

Top 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, 274 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
The stone exterior of the cottage features a muted color palette, complemented by flowering plants and neatly arranged outdoor seating. A grey door serves as a focal point, framed by two windows that allow natural light to enter the space.
Cottage in Barnard Castle
4.98 out of 5 average rating, 128 reviews

Phil's Cottage. Sleeps 2 maximum 1 dog

Phil's Cottage is a beautiful one bedroom stone cottage with stunning countryside views. The cottage is a recently refurbished barn conversion ideally located just 2 miles from the historic market town of Barnard Castle. The property offers plenty of private parking, and outdoor seating area to the front and pretty courtyard to the rear with outdoor seating . Dogs are subject to an additional £25 per stay. Maximum one fully house trained well behaved adult dog by prior permission from owners.

Guest favourite
A cozy living area features a colorful patchwork sofa with decorative cushions, set against neutral walls. The compact kitchen is visible with grey cabinetry and shelves containing spices. A wooden coffee table sits in front of the sofa, and a mirror enhances the natural light.
Cottage in North Yorkshire
4.92 out of 5 average rating, 681 reviews

Entire Home Bargate Little cottage with log burner

Cozy one bedroom Cottage with log burner; located just down the hill from Richmond Market Place. One bedroom upstairs. Kitchen, diner and lounge are all the same area with a sofa bed on the ground floor. Underfloor heating downstairs. Bedding and towels are provided for guests. Plenty of walks directly from the cottage the river being just around the corner. The castle walk is 2 minutes away. Pubs and restaurants within walking distance. Richmond has everything you need for a fabulous break.

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
4.97 out of 5 average rating, 128 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.

Top guest favourite
A peaceful outdoor area is captured, featuring two slender trees with a green tarp draped between them. A wooden platform provides seating space, with a small lantern placed on it. In the background, a quaint cottage is visible, adorned with a tiled roof and a window featuring a flower box.
Tiny home in County Durham
4.99 out of 5 average rating, 283 reviews

Fairbeck an idyllic & romantic woodland retreat

A charming, and beautiful cottage set within a courtyard in an idyllic ten acre woodland location. The cottage is every inch the beautiful setting for a romantic break away. The outside area of the cottage includes a raised platform & fire pit for your own use. Whilst it appears to be set in a remote rural location, it is in fact incredibly well-situated to be able to visit local attractions whilst being easily accessible from the main road: A1M . “A hidden gem definitely worth staying here!”

Top guest favourite
The exterior of a stone cottage is depicted, showcasing a rustic facade with large windows and a slate roof. Surrounding greenery and a gravel area create a welcoming entrance.
Cottage in Cotherstone
4.97 out of 5 average rating, 128 reviews

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.

Guest favourite
A serene riverside scene captures the flowing River Tees, with smooth rocks partially submerged in the water. In the background, the rustic cottage is surrounded by lush greenery, while a gentle waterfall cascades over stones, creating a tranquil atmosphere.
Cottage in Barnard Castle
4.94 out of 5 average rating, 110 reviews

Riverview Cottage- Overlooking the Tees -Superhost

This relaxing riverside cottage combines oodles of charm with breathtaking views of the River Tees and easy access to the historic market town of Barnard Castle (locally known as Barney). Step straight out of the front door onto the Teesdale Way, one of the many rural footpaths crisscrossing this beautiful, largely undiscovered part of the country. Or take a short stroll into Barnard Castle to discover its rich heritage and enjoy the warm hospitality of its many cafes, bars, and restaurants.

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.
Flat in Gainford
4.92 out of 5 average rating, 258 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
4.92 out of 5 average rating, 159 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 £30/sty

Top guest favourite
A wooden balcony overlooks a serene lake surrounded by lush greenery. Tall trees frame the scene, and gentle ripples can be seen on the water's surface, creating a peaceful natural backdrop.
Barn in Ravensworth
5 out of 5 average rating, 197 reviews

The Lake House

The detached Lake House is set in 11 acres. Ravensworth is an enchanting village with many of the houses dating from the 17th century. The village is defined by its green, and ancient ruined castle, only a few miles from the pretty towns of Richmond and Barnard Castle . A village pub and two wonderful farm shop cafes within walking distance. The Lake House has uninterrupted views of the lake and surrounding woodland. The Lake House can also be booked together with Willow Cottage.

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
4.94 out of 5 average rating, 170 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.

Popular amenities for Winston holiday rentals

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  2. United Kingdom
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  4. County Durham
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