Cottage holiday rentals in Helmsley

Cosy ‘Cobblers Cottage’ - Pickering

Enjoy easy access to everything from our perfectly located, traditional stone home on the gateway to the North York Moors National Park. Just steps away from Pickering town centre with an array of shops, pubs, cafes, bars, restaurants, bakers, butchers & takeaways on offer. A short stroll to the North Yorkshire Moors Railway giving pleasant & easy access to Whitby, Goathland, Levisham, Newtondale and Grosmont. Also perfectly located for Scarborough, Whitby, Malton, Helmsley & Dalby Forrest.

Cosy character cottage in heart of Pickering

31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, steam railway, the coast and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

Apple Tree Cottage. Stokesley.North Yorkshire.

A delightful old cottage overlooking West Green with a mix of antique, upcycled and vintage inspired decoration. The cottage is dog friendly, with a patio and large enclosed, secure garden. Located on the outskirts of the historic market town. The town has a distinguished wide cobbled high street lined with Georgian and Victorian buildings. It is served by banks,shops, up market restaurants and pubs. Surrounded by the Yorkshire Moors it makes an ideal base for exploring the Dales & East coast.

The Owlets, Ampleforth

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

The Smithy at Cross Pipes, Goathland

The Smithy is a self contained stone built cottage situated on the edge of the beautiful North Yorkshire Moors. It was built in the 1800’s and was originally one of two blacksmiths serving the community of Goathland. The Smithy offers you a comfortable base to visit the local area. Spacious studio accommodation with a king sized bed in a recessed area, walk in shower and toilet, full kitchen facilities, wood burning stove, TV and Wi-Fi. There is an outside seating area and private parking.

The Cobbler's Cottage

Nestled in the scenic North Yorkshire village of Sessay, this charming former cobbler's cottage offers a spacious retreat. Inside, you'll find a wood-burning stove, TV, Blu-ray player, and a modern kitchen equipped with an oven, microwave, dishwasher, fridge freezer, Nespresso coffee maker, and a washing machine. Step outside to a private patio complete with a dining area and barbecue. Plus, we warmly welcome one well-behaved pet, so you can bring your furry friend along if you desire.

Luxury By The Brook

Sally’s Nook is a beautiful bolthole by the brook in the village of Hebden in the heart of the Yorkshire Dales. The cottage is newly renovated to a very high standard and perfect if you want to treat yourself to a luxurious few days or week in the Dales . There is a well equipped handmade kitchen , a log burner, exposed beams ,kingsize bed , freestanding bath , parking , smart TVs , WiFi and outside space by the brook . Idyllic location with walks and cycling on the doorstep .

Goose End Cottage, North Yorkshire

Take a break and unwind in a characterful cottage set in beautiful countryside. This 18th century grade-II listed property is right beside the River Seven, in the picturesque village of Sinnington, and the North York Moors National Park. The cottage is full of original character, whilst having all the amenities needed for a relaxing break. Many amazing walks can be enjoyed from right outside the door and the wonderful village pub and restaurant is only a few minutes walk away.

The Shepherds Cottage, Stillington, York

Nestled in the charming village of Stillington near York, this cosy cottage offers a peaceful countryside escape. Relax by the log-burning stove or stroll to one of two friendly local pubs serving delicious food. For nights in, enjoy a village takeaway. Surrounded by scenic walks and just 10 miles from York’s historic centre, it’s ideal for exploring. Helmsley’s lovely market town is close by too. Perfect for couples or small families—well-behaved dogs are warmly welcomed.

Historic cottage, wood-fired hot tub + village pub

Three hundred year old sandstone, exposed timber beams, and the kind of warmth that comes from old walls, open fires and underfloor heating. Yew Tree Cottage @ Kingfisher and Yew sits opposite a dog-friendly village pub. Take long walks from the front door. Light the wood-fired hot tub in the walled garden and toast your toes by the fire. This Grade II listed cottage is seven minutes from the market town of Malton. Featured in Living North's top self catering retreats.

Whootin Owl Barn

Whootin Owl Barn is a smart luxury detached barn with private screened hot tub and gravelled fire pit area overlooking private woodland on a tranquil country lane in the heart of North Yorkshire only 9 miles from Castle Howard and 30 mins from York City Centre. If you are looking for a romantic modern and ultra clean property in a beautiful private location for a short break or Holiday getaway or looking for a base to explore North Yorkshire, look no further.

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set within the 220 acres with stunning countryside views you’re sure to feel relaxed from the minute you arrive. Cecil cottage sleeps up to 5 guests and has a fully equipped kitchen, modern bathroom which has a shower/bath located downstairs. There is also a wood burner and an enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.