Pickering is an ancient market town on the southern edge of the dramatic North York Moors. 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. Holiday cottages in Pickering tend to be within a comfortable stroll of the town centre, which is home to a number of cosy pubs and excellent eateries – including Willowgate Bistro, Feast and local favourite Capplemans Fish and Chip Restaurant. At the heart of Pickering is a pretty marketplace, where a variety of 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 and in 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.

25 cottages found 25 match all criteria.

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 spacious, traditional Farmhouse making a marvellous base for families or friends. Pets welcome.

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.

One of nine countryside cottages that make up Keid Head Farm Cottages and nestled near the foot of rolling moorlands, Pigeon Cote near the market town of Pickering, North Yorkshire, retains much of its original charm and features, with open beamed ceilings and traditional stone fireplace.

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.

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.

Mallard Cottage is one of 4 pet friendly holiday properties in the pretty North York Moors village of Newton-on-Rawcliffe. The property has 3 bedrooms on 2 floors. The first floor, comprising sitting room, kitchen/dining room, twin bedroom and wet room, is suitable for full-time wheelchair users.

The Old Coach House in the picturesque North York Moors village of Thornton-le-Dale, North Yorkshire, affords families and small groups spacious and comfortable holiday accommodation. This popular countryside cottage boasts vaulted ceilings, exposed beams and a superb open-plan living area.

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.

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

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

1 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 and a cast iron and marble fireplace, plus a furnished sunny patio, and an open fire.

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.

Magnificent rural views fill the large windows of the conservatory at Woodlea, a large holiday cottage in Pickering near Rosedale Abbey on the North York Moors. An open fire adds rural charm to the large sitting room of the four-bedroom tastefully decorated, pet-friendly cottage in North Yorkshire.

Gateside is a lovely stone-built barn conversion that overlooks the village green of Newton-on-Rawcliffe, North Yorkshire, a child-friendly cottage that offers upside-down accommodation in the Ryedale district with a well-equipped kitchen, spacious sitting room and three bedrooms.

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

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.

The Old Vicarage is an impressive detached property with lots of space, including four reception rooms. Set in a large, lawned garden, the property is in the heart of the North Yorkshire Moors on the edge of the beautiful village of Rosedale Abbey.

Housing a four-poster bed, beamed ceilings and traditional fireplace, Wheelhouse Cottage is an authentic Yorkshire cottage near Pickering. The award-winning property at Keld Head Cottages boasts a stone façade, beautiful views, extensive gardens, indoor and outdoor play areas for children.

The Granary is a detached, Grade II listed rural cottage on Keld Head Cottages near Pickering in Yorkshire. The award-winning property treats guests to open fire, exposed beams, large gorgeous gardens and indoor and outdoor play areas, and boasts enviable views which guarantee relaxation for all.

'Granary' is a first floor, pet friendly countryside apartment with access to a indoor heated pool, hot tub, and sauna in Newton-on-Rawcliffe, Pickering. This cosy apartment has been attractively adapted, having an open plan lounge/kitchen/diner, with views to the Vale of Pickering and beyond.

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

Mel House Cottages are a group of 4 pet friendly properties sleeping from 3 to 19 Guests at 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: Indoor Pool, Hot Tub, and Sauna.

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 ideally situated for a holiday enjoying both the moors and the coast.

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 and contemporary interior, plus a delightful garden and open-plan design, all in the heart of the North York Moors and Coast.

A stay in a Pickering holiday cottage 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 breath-taking scenery. Enjoy an unforgettable meal on the Pullman Dining Train, while 24 miles of glorious countryside float by. Trains run regularly from Pickering to Grosmont – and as far as the coastal town of Whitby during the summer. 

If you want to explore the windswept beauty of the North York Moors National Park, holiday cottages in Pickering are perfectly 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.