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
8
Bedrooms
4

Pasture View Cottage is a large eco-friendly, single-storey country cottage on the edge of Pickering for holidays exploring the North York Moors and the North Yorkshire coast. Features include a large private garden and a very well-equipped kitchen. Children will love the play area and play shed.

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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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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
2
Bedrooms
2

Mill Cottage is a multi-award-winning property set on Keld Head Cottages near Pickering in North Yorkshire. The stone-built rural cottage has been carefully refurbished with traditional features and modern comforts and boasts gorgeous gardens, large indoor and outdoor play areas and lovely views.

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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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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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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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Sleeps
10
Bedrooms
4

Boundcliffe is a large holiday cottage in a rural location on the North Yorkshire Moors. Sleeping ten people in four bedrooms in the village of Allerston near Pickering, Boundcliffe is a spacious, traditional Farmhouse making a marvellous countryside base for families or friends. Pets welcome.

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A holiday cottage lounge with sofa, coffee table and wide-screen tv.
Sleeps
6
Bedrooms
3

Mallard Cottage is a lovely holiday property in the charming village of Newton-on-Rawcliffe in the North York Moors. The property is pet-friendly and offers four different accommodation options. It features three bedrooms spread over two floors. The cottage's first floor, which includes a sitting room, kitchen/dining room, twin bedroom, and wet room, is perfect for wheelchair users. It is designed to comfortably accommodate full-time wheelchair users.

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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.