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.

Barn conversions in a courtyard overlook a raised flower bed in its centre
Sleeps
5
Bedrooms
2

Tucked in near the Great Fryup Dale in the heart of North York Moors National Park, The Byre in the civil parish of Danby, North Yorkshire, sits on a working organic farm, a two-storey countryside cottage featuring exposed beams, vaulted ceiling, and ground floor underfloor heating.

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An indoor heated swimming pool at a Pickering holiday cottage
Sleeps
5
Bedrooms
3

Swift Cottage is a charming 3-bedroom ground floor cottage sleeping 5 with the use of an outdoor heated pool. The cottage has an easy-access wet room with rails and a mobility chair, so accessible for guests with disabilities. Swift is in the North York Moors National Park. Pets welcome.

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A large, single storey barn conversion overloks a lawn.
Sleeps
7
Bedrooms
3

Find warm accommodation for your Yorkshire holiday at The Stables at Keld Head Cottages, one of nine traditional cottages on the edge of the market town of Pickering, North Yorkshire, retaining much of the converted stone-built barn’s original features, with open beamed ceilings and stone fireplace.

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A chapel conversion with a large rose window sits behind a low stone wall.
Sleeps
8
Bedrooms
4

The Old Methodist Chapel is a sophisticated conversion of the old chapel in Rosedale Abbey. Set amid the North York Moors and Coast, the cottage features tall arched windows, exposed timbers, stripped pine doors, a cast iron and marble fireplace, a furnished sunny patio, and an open fire.

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Sleeps
4
Bedrooms
2

The Coach House offers sophisticated coast and country accommodation for four in the North Yorkshire village of Levisham. It boasts subtle elegance with a stone exterior, a contemporary interior, and a delightful garden and open-plan design, all in the heart of the North York Moors and Coast.

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Single storey of a barn conversion overlooking a lawn on a North Yorkshire farm.
Sleeps
2
Bedrooms
1

The Smithy at Keld Head Cottages is a quaint romantic cottage on a gorgeous property outside Pickering in North Yorkshire. The rural holiday cottage boasts exposed beams, a traditional fireplace, award-winning gardens, beautiful views, and extensive indoor and outdoor play areas.

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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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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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A heated indoor swimming pool with a hot tub.
Sleeps
3
Bedrooms
2

Granary is a pet-friendly countryside apartment located on the first floor with access to an indoor heated pool, hot tub and sauna in Newton-on-Rawcliffe, Pickering. This cosy apartment has an open-plan lounge/kitchen/diner, providing stunning views of the Vale of Pickering and beyond. It has been attractively designed to make your stay comfortable and enjoyable.

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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.