Tucked beneath the historic Pickering Castle and built into the natural rockside, Rockside is a beautifully styled cottage that blends colourful country interiors with a truly unique setting. Sleeping up to six guests, this charming retreat is perfect for families or friends looking to enjoy a relaxed stay in one of North Yorkshire’s most characterful market towns.
The interiors are best described as colourful country, full of warmth, charm and personality. Downstairs, a cosy snug lounge provides the perfect spot to curl up with a book or enjoy a quiet moment, while the main living space opens up into a large living-dining room designed for socialising. Here you will find a generous L-shaped sofa, a farmhouse-style dining table for gathering together, and a welcoming atmosphere that makes it easy to settle in. The kitchen is equally impressive, featuring sleek marble surfaces and everything you need for effortless entertaining.
Upstairs, Rockside offers three thoughtfully designed bedrooms, including two king-size rooms and one twin. One of the king rooms features its own ensuite, while the remaining bedrooms are served by a spacious family bathroom complete with a freestanding roll-top bath and separate shower – ideal for long, indulgent soaks after a day of exploring.
The garden at Rockside is something truly special. Set across tiers carved into the rockside, each level offers its own unique perspective. At the top, you can enjoy elevated views across the heritage railway, where the occasional steam train passes by – a nostalgic and unforgettable sight. The lower terrace is made for relaxed outdoor living, with space for alfresco dining, a BBQ and a hot tub perfectly positioned for soaking under the stars. All the while, Pickering Castle provides a striking backdrop, visible from every corner of the garden.
Located in the heart of Pickering, you are perfectly placed to explore the North York Moors, the nearby coastline, and the town’s independent shops, cafes and historic attractions. Whether you are hopping on the North Yorkshire Moors Railway, walking through rolling countryside or simply enjoying the view from the garden, Rockside offers a stay that feels both peaceful and full of character.
OTHER THINGS TO NOTE
GROUND FLOOR
Entrance hall leading to open plan sitting room and dining area, smart tv and log burner
Snug with comfy sofas and smart tv
Two steps up to kitchen and door to outside.
FIRST FLOOR
Master bedroom with king sized bed and ensuite shower
Two further bedrooms one with king sized bed and one with twin beds
Family bathroom with roll top bath and separate shower
GARDEN
Large tiered private walled garden with hot tub and outdoor seating.
Located in the heart of Pickering, you are perfectly placed to explore the North York Moors, the nearby coastline, and the town’s independent shops, cafes and historic attractions. Whether you are hopping on the North Yorkshire Moors Railway, walking through rolling countryside or simply enjoying the view from the garden, Rockside offers a stay that feels both peaceful and full of character.
Share Property:








A beautiful newly interior designed Yorkshire holiday home in Pickering for six guests with hot tub and garden.







A beautiful four-bedroom Yorkshire stone hideaway in the heart of Osmotherley Ideal for family time & relaxing stays.







A charming three-bedroom holiday cottage nestled in the rural heart of North Yorkshire. Overlooking a tranquil village pond.
We want you to find the perfect Yorkshire Escape