Stokesley is a pretty North Yorkshire market town on the edge of the North York Moors National Park. Just 30 miles from the coast and 10 miles from bustling Middlesbrough, it is perfectly located for discovering North Yorkshire. Known as a gateway to the North York Moors, this picturesque market town is full of Georgian and Victorian architecture and lies on the banks of the River Leven. Five miles from holiday cottages in Stokesley is the Captain Cook Monument, a 51-foot obelisk visible for miles around. The nearby village of Great Ayton was the childhood home of Captain James Cook, the British explorer and navigator who achieved the first recorded circumnavigation of New Zealand. 

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The White Swan, a lively local pub, is a stone’s throw from your holiday cottage in Stokesley. Choose from a selection of local beers and ales, brewed at The Captain Cook Brewery, which was established by the pub’s landlord in 1999. For lunch, Chapters Deli, Bistro and Wine Bar occupies a 16th century building and serves a menu inspired by foods from around the world. Self-catering holidays in Stokesley would not be complete without a day out on the dramatic North York Moors. Covering 554 square miles, the landscape ranges from deep wooded valleys to vast expanses of heather moorland.

Explore the moors via the 1,400 miles of walking routes, or traverse the landscape from a mountain bike or on horseback. Look out for resident and migratory birds, such as the golden plover, lapwing, red grouse, and short-eared owl. The vibrant coastal town of Whitby is just 30 miles from Stokesley. Divided by the River Esk, the town is best-known for the ruins of Whitby Abbey, which inspired Bram Stoker’s Dracula. Pick up a portion of fish and chips and enjoy a day out at this traditional seaside resort.

Five miles along the coast, the village of Ravenscar is home to 300 seals. The famous rocky headland faces Robin Hood’s Bay, a small fishing village set on a rugged stretch of coast.