Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Guest favorite

Cottage in Gainford

4.97 out of 5 average rating, 185 reviews

Cosy Cottage

This is a lovely 2 bedroom cottage that has just been fully renovated. It can sleep upto 6 people as it has 2 bedrooms and a double sofa bed in the living room. There is fast wi-fi and smart TV. A range cooker, microwave, kettle, toaster & washing machine in the kitchen. There is also a travel cot, high chair & safety gate if needed. Gainford village is an ideal location to start a hike or bike ride from and the river Tees is a 2min walk. Bus stops are 20m from the front door to get you to town.

Nov 30 – Dec 7

G$32,459 GYD per night

Guest favorite

Cottage in West Auckland

4.96 out of 5 average rating, 182 reviews

No 6, stylish and comfortable get away and relax.

Recently refurbished miners cottage in the hamlet of Hummerbeck, light and bright offering great comfort and easy access to many local attractions. Close to all the major supermarkets gives plenty of choice. Enjoy a little luxury with our superking master bedroom with the versatility of twin beds and sleeping up to six guests with a quality sofa bed. Perfect for a short break, holiday or business trip. Your dog is welcome too so the whole family can come. Parking is directly opposite the cottage

Nov 27 – Dec 4

G$15,839 GYD per night

Guest favorite

Guest suite in Gainford

4.95 out of 5 average rating, 101 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

Jan 3 – 10

G$20,286 GYD per night

Guest favorite

Vacation home in County Durham

4.91 out of 5 average rating, 155 reviews

Luxury townhouse in Barnard Castle, 2 Bed,sleeps 4

The Retreat is a stylish and luxurious holiday home in the heart of Barnard Castle. Perfect for those looking to enjoy a relaxing escape, whilst enjoying local walks and stunning landscapes. Get ready to fall in love with this immaculate hideaway, which offers comfortable accommodation along with dining pubs and restaurants on the doorstep. The house is fitted with high quality appliances such as dishwasher, washing machine, fridge/freezer, microwave, sage coffee machine, WiFi and TV.

Oct 6 – 13

G$24,295 GYD per night

Guest favorite

Loft in North Yorkshire

4.99 out of 5 average rating, 182 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.

Dec 6 – 13

G$18,986 GYD per night

Guest favorite

Cottage in Gainford

4.97 out of 5 average rating, 188 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 double ended roll top bath situated in the master bedroom along with a four poster bed, fully equipped kitchen, private yard to the rear & log burner in the living room to give that real country cottage feel along with exposed beams Comes with WiFi, Netflix and a pub just a stones throw away

Jul 30 – Aug 6

G$29,027 GYD per night

Guest favorite

Cottage in North Yorkshire

4.99 out of 5 average rating, 188 reviews

The Barn at Cocker House in the heart of the Dales

Welcome to The Barn! Our charming 1-bedroom Cottage in Arkengarthdale offers breathtaking countryside views, perfect for couples or outdoor enthusiasts exploring the Yorkshire Dales. Immerse yourself in the beauty of rolling hills, lush fields, and meandering rivers. Take leisurely strolls or challenge yourself with hikes. The Barn provides a tranquil retreat with cozy ambiance and well-equipped amenities. Create lasting memories in this idyllic corner of Arkengarthdale.

Apr 3 – 10

G$29,301 GYD per night

Guest favorite

Farm stay in Cowshill

4.97 out of 5 average rating, 216 reviews

Romantic Off-grid retreat in North Pennines AONB

Low Moss Cottage. A cute and cosy, recently renovated, totally off-grid holiday cottage with dramatic and stunning views of Weardale. On a hill away from other houses and distractions, this 18th century cottage is the perfect place to gaze into the dark skies while cuddled up by the fire, or soak in the window side bath. Perfect for walkers, artists, photographers, writers, digital detoxers, honeymooners and anyone who wants to get away from it all.

Mar 20 – 27

G$26,074 GYD per night

Guest favorite

Cottage in Middleton-in-Teesdale

4.98 out of 5 average rating, 252 reviews

Simply Stunning Ash Cottage, quiet & cosy

Ash Cottage is a delightful, characterful cottage situated in a prime, quiet location in the heart of Middleton in Teesdale, an area of outstanding natural beauty. Middleton in Teesdale is a small market town in County Durham, which is situated on the North side of Teesdale, a few miles north-west of Barnard Castle. Middleton in Teesdale is on the Pennine Way about 4 miles from High Force Waterfall.

Feb 12 – 19

G$26,162 GYD per night

Guest favorite

Home in Cockfield

4.98 out of 5 average rating, 331 reviews

Modern Cottage with hottub in Peaceful Area

Beautiful little cottage with a hottub and modern interiors. Great sized garden, perfect for use with the BBQ. Brilliant location within Teesdale. Hamsterley Forest, Raby Castle, Barnard Castle, High Force, Bishop Auckland and Kynren all within a short drive. With a ten minute walk to Cockfield, there is a friendly local pub, shops, butchers, takeaway and newsagent.

Jan 9 – 16

G$37,006 GYD per night

Guest favorite

Cottage in Richmond

4.88 out of 5 average rating, 121 reviews

Merok Cottage, Newsham, North Yorks

Merok Cottage is a comfortable two bedroom holiday cottage, sleeping up to 4 guests, in a quiet village in Teesdale, between Barnard Castle and Richmond, on the edge of the Yorkshire Dales National Park. Stay for a week's holiday or longer, use as a peaceful base to work away from home, or take a short break from Friday to Monday or Monday to Friday.

Aug 5 – 12

G$22,323 GYD per night

Guest favorite

Apartment in Richmond

4.98 out of 5 average rating, 535 reviews

Limekilns Annexe Nr Barton MiddletonTyas Richmond

Recently refurbished self-contained annexe on a small holding between the villages of Middleton Tyas and Barton. One mile from Scotch Corner, six miles from Richmond and Darlington. With its own entrance, it comprises a spacious open plan sitting/dining/ kitchen area and ensuite bedroom. Sleeps two adults in a king- sized bed.

Oct 18 – 25

G$24,968 GYD per night