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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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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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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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 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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Sleeps
44
Bedrooms
20

In the open countryside on the edge of Pickering and the York Moors, a picturesque group of stone cottages with beamed ceilings and stone fireplaces furnished with an emphasis on comfort and relaxation. Extensive gardens with a garden house, play area and barbecue. See our website for Virtual Tour www.keldheadcottages.com

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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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A semi-detached cottage overlooks a stone-walled front garden.
Sleeps
4
Bedrooms
2

The quaint Grade-II listed Croft Head Cottage boasts exposed beamed ceilings, flagged floors and a wood-burning stove in a converted coaching inn close to the village of Wrelton in the North York Moors. The pet-free property welcomes families with two bedrooms and cast-iron furnishings.

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An indoor heated pool with a surrounding terrace. Floor-to-ceiling windows line one side.
Owl
Sleeps
4
Bedrooms
2

Owl is a two-bedroom apartment on the ground floor beneath Granary. The apartment has two bedrooms, a double and a twin and an open-plan living area with a fitted kitchen, lounge and dining area. The apartment also has a shared indoor heated pool, spa, and sauna. Well-behaved dogs welcome.

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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.