Cottage holiday rentals in Helmsley

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.

Historic cottage, log-burning tub & village pub

Unwind in this beautifully restored Grade II listed, 17th Century farmers cottage with exposed beams, original ironwork, underfloor heating and a soothing log burning hot tub. Opposite you'll find a cosy, dog-friendly village pub with open fires. You’ll be 7 minutes away from artisanal food producers in the market town of Malton (known as Yorkshire's Food Capital) and ideally located for exploring the Yorkshire Wolds (2 miles), Howardian Hills (10 miles), York (17 miles) & Beaches (27 miles).

Grooms Cottage by Sheriff Hutton Castle Near York

Grooms Cottage is on a private estate right next to the ruins of Sheriff Hutton Castle. The property is in a peaceful setting but only two minutes walk away from the village pub and post office/general store. Our cottage was completely renovated in 2021 and is in a great location for walkers, cyclists, and explorers. It’s about 10 miles from both York and Malton, Castle Howard is under 6 miles away, and the coast can be reached in under an hour. Grooms Cottage sleeps 4 guests+2 babies +dogs

Charlie’s barn. A stunning barn conversion

Unwind in our stunning 18th century, 1 bed barn conversion with beamed ceilings and open plan living space. Outside there is a south facing secure court yard with your own private access. Situated in a tranquil village within an area of outstanding natural beauty. The village boasts a fine dining pub with other local pubs within a short distance or even visit Malton the food capital. A perfect base for biking , walking or visiting Castle Howard, the North Yorkshire moors , East coast or York.

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.

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.

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.

Cottage in North Yorkshire

Tarrs Yard is a beautifully restored early 18th century cottage, nestled in the valley between York and Malton. Ideal for walkers and nature lovers, the cottage is just a short drive from Castle Howard and close to the North Yorkshire Moors, Dalby Forest and the Yorkshire Coast. In a picturesque setting surrounded by uninterrupted views of the Howardian Hills and the Yorkshire Wolds, the cottage is perfectly positioned to enjoy the best of the great outdoors.

Cosy barn*York*Yorkshire Countryside*Coas

Set in the countryside within easy reach for pretty towns, the coast, York and various attractions, you will find "The Byre". This self-contained, barn with traditional beams, underfloor heating, and special touches, offers a relaxing retreat after a long day exploring. Your stay is made that little extra special...you can put your feet up with a Nespresso coffee, a boxset on Netflix or music on the Bose. Or now enjoy the sun in theprivate garden.