This charming market town lies on the edge of the North York Moors National Park. With access to some of the most breathtaking landscapes of mile after mile of rolling heather moors, right on your doorstep. With its fascinating history, many of the buildings date back to the 17th century, the town's medieval castle dominates the skyline high up on its grassy knoll. Sit back and relax in one of the cosy pubs or inns that surround the town square. If the weather is being kind take a dip in the town's open-air swimming pool. Explore our selection of Helmsley cottages to find the perfect break for you and your family. Needing suggestions for things to see and do? Scroll down for our top 5 activities in the area.