A locomotive hauls a carriage set through open countryside.

Find My Favourite Holiday Cottages in Pickering

Pickering is an ancient market town on the southern edge of the dramatic North York Moors. Holiday cottages in Pickering tend to be within a comfortable stroll of the town centre, which is home to several cosy pubs and excellent eateries – including Willowgate Bistro, Feast and local favourite Capplemans Fish and Chip Restaurant. With its famous Medieval wall paintings, traditional railway and stunning views across the Vale of Pickering, this traditional community has plenty to offer visitors. Pickering is the perfect base for experiencing life in an authentic Yorkshire town and exploring some of the region’s most impressive countryside. At the heart of Pickering is a pretty marketplace where various independent businesses sell everything from fresh, local produce to gifts and antiques.

The North Yorkshire town of Pickering is situated on the edge of the North Yorkshire Moors, between the towns of Scarborough, Whitby, Helmsley and Malton and is often referred to as the “Gateway to the North York Moors”. The scenery around Pickering is spectacular, and it’s not just about the Moors. The region is full of historical places of interest and ancient Abbeys and houses to explore.

Sleeps
2
Bedrooms
1

The compact and cosy Stable Cottage lies within the stone walls of a converted stable and offers a delightfully-appointed rural retreat on a working farm in Levisham. The pet-friendly holiday cottage near Pickering is ideal for a holiday, enjoying both the moors and the coast.

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Sleeps
5
Bedrooms
2

Wheelhouse Cottage is an authentic Yorkshire cottage near Pickering. It has a four-poster bed, beamed ceilings, and a traditional fireplace. The award-winning property at Keld Head Cottages boasts a stone façade, beautiful views, extensive gardens, and children's indoor and outdoor play areas.

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Barn conversions overlook a courtyard with a central flower bed
Sleeps
4
Bedrooms
2

The Granary is a charming, detached cottage located in the rural area of Keld Head Cottages, near Pickering in Yorkshire. This award-winning farm cottage features an open fire and beautiful exposed beams, creating a warm and cosy ambience. The cottage also offers large, stunning gardens with indoor and outdoor play areas, perfect for a relaxing and enjoyable stay. The beautiful views surrounding the cottage are sure to help you unwind and enjoy a peaceful time away from the hustle and bustle of everyday life.

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2-storey exterior of. stone-built barn conversion overlooking a paved terrace and a lawn
Sleeps
2
Bedrooms
1

Harvest Cottage welcomes couples to a pretty stone and pantiled farm cottage near Pickering in the heart of picturesque Levisham. The pet-friendly, one-bedroom barn conversion offers ample gardens and peace and quiet. It is an ideal base for exploring the North York Moors and coast.

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Stays in Pickering holiday homes would be incomplete without a trip to one of the town’s most celebrated historical attractions, the 15th-century wall paintings at St Peter and St Paul’s Church. Nearby is the imposing motte-and-bailey fortification of Pickering Castle, which dates back to the days of William the Conqueror and is open for visitors to explore. Taking a ride on a North Yorkshire Moors Railway steam locomotive is a magical way to experience the area’s breathtaking scenery. Trains run regularly from Pickering to Grosmont – and as far as the coastal town of Whitby during the summer. Enjoy an unforgettable meal on the Pullman Dining Train while 24 miles of glorious countryside float by. 

If you want to explore the windswept beauty of the North York Moors National Park, holiday cottages in Pickering are ideally located at the southern boundary. Wild moorlands, ancient abbeys, tumbling rivers and pretty villages can all be found in the park, which is a long-running favourite among ramblers and wildlife watchers.