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
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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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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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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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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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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A lounge with armchairs, oak-beamed ceiling and a staircase.
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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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
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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A heated indoor pool and large jacuzzi.
Sleeps
19
Bedrooms
10

Mel House Cottages are a group of four pet-friendly properties that sleep from 3 to 19 Guests in the centre of attractive Newton-on-Rawcliffe in the North York Moors. Three of the four properties are rated at various levels of accessibility for disabled use. Facilities include an indoor Pool, Hot Tub, and Sauna.

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  • Walking Holidays

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.