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.

Exterior of a large barn conversion with external steps to 1st flor front door - facing a mature garden
Sleeps
4
Bedrooms
2

The upside-down design of Barn Cottage captures the beautiful views of the Yorkshire countryside and adds another feature to this award-winning holiday cottage near Pickering. The rural cottage offers extensive manicured gardens with multiple play areas and spaces to entertain, relax and truly unwind.

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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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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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A large, single storey barn conversion overlooks 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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Exterior of a barn conversion overlooking a garden courtyard
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 twin-gabled brick holiay home overlooking a guest car-parking area
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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Sleeps
10
Bedrooms
4

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

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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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A spacious, oak-beamed lounge area with sofas, TV, wood burner and dining table.
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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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.