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.

The Stables cottage in Snainton Nr Pickering, North Yorkshire
  • Sleeps 4
  • Bedrooms 2

The Stables Cottage is a detached holiday cottage near Snainton in North Yorkshire, offering easy access to the North York Moors National Park, Dalby Forest and the Yorkshire coast. Sleeping up to four guests, it's well suited to couples, families and friends looking for a self-catering base close to Pickering, Scarborough, Whitby and many of the region's walking, cycling and sightseeing attractions.

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Granary Cottage sleeps 4 Snainton Nr Pickering North Yorkshire
  • Sleeps 4
  • Bedrooms 2

Granary Cottage is located near the village of Snainton in North Yorkshire, within easy reach of the North York Moors National Park and the Yorkshire coast. From here, guests can explore walking and cycling trails, visit market towns including Pickering and Malton, or spend a day by the sea in Scarborough, Filey or Whitby. Its central location makes it a good base for discovering many of North Yorkshire's best-loved countryside and coastal attractions.

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  • 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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  • Sleeps 16
  • Bedrooms 8

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.

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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 a Virtual Tour.

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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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  • 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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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 near 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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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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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 unwind.

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Exterior of a long, many-windowed barn conversion to form a single-storey holiday cottage in Pickering.
  • 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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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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  • Sleeps 4
  • Bedrooms 2

Owl is a two-bedroom apartment on the ground floor beneath Granary. It 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 are welcome.

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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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Exterior ofa barn conversion behind a shrub-filled garden.
  • Sleeps 5
  • Bedrooms 2

One of nine countryside cottages that make up Keld 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.

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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.