Helmsley is a medieval market town in Yorkshire’s unspoiled Ryedale district. It lies on the southern boundary of the North York Moors National Park, where the dale leaves the moorland and meets the flatter scenery of the Vale of Pickering. From your holiday cottage in Helmsley, a short stroll will bring you to the town centre, much of which is a conservation area, thanks to its unique historic landmarks. A maze of pretty streets surrounds the marketplace, lined with a selection of independent shops, including Room for Antiques and Bondgate Antiques. Thomas the Bakery has a reputation for delicious treats, and Helmsley Brewing Co. is the place to go for craft beers. You’ll also find some of the region’s best eateries, where you can enjoy delicious food, prepared with fresh ingredients from the surrounding fields. From beautiful gardens to live entertainment, there’s no shortage of things to do on self-catering holidays in Helmsley. Check out Helmsley Arts Centre for live music, comedy, films and art exhibitions

2 cottages found 2 match all criteria.

The Old Cart House is a luxury barn conversion, situated on a hill farm in Farndale near Helmsley, within the North York Moors. A truly stunning renovation from top to bottom, the residence boasts top of the range decor throughout and contemporary finishes, perfect for group and family holidays.

Castle View is a tastefully furnished, large, family friendly village holiday cottage in Helmsley in the heart of the North York Moors National Park -and also within an easy drive of the coast. This dog friendly cottage sleeps 11 in 4 bedrooms.

Visible from most Helmsley holiday cottages, Helmsley Castle looms over the town. Reserve an hour or two to discover how the castle evolved over the centuries, from a medieval fortress to an extravagant Tudor mansion. Nearby, the ancestral home of the Earls of Feversham, Duncombe Park, is a magnificent stately home, surrounded by 30 acres of stunning gardens. The ruins of Byland and Rievaulx nestle in neighbouring valleys, surrounded by tranquil countryside full of birdsong.

A stone’s throw to the north of Helmsley, the North York Moors National Park is a paradise for walking, horse-riding and wildlife-watching. This expanse of high, heather moorland and lush, green valleys is crisscrossed by scenic footpaths which follow the routes of ancient roads. If you fancy a day on the beach, the classic resort of Scarborough is less than an hour’s drive eastward, on the A170. 24 miles north of Helmsley, York is a fascinating city with some of England’s most impressive architecture.