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.

Barn conversions in a courtyard overlook a raised flower bed in its centre
Sleeps
5
Bedrooms
2

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.

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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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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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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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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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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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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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An indoor heated pool with a surrounding terrace. Floor-to-ceiling windows line one side.
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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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.