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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.
![A spacious, oak-beamed lounge area with sofas, TV, wood burner and dining table.](/sites/default/files/styles/gallery_thumbnail/public/cottage/2024-06-28/1-swift-holiday-cottage-in-pickering-oak-beamed-lounge.jpeg?h=82f92a78&itok=V3JOqged)
- 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
- 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.
![A lounge with armchairs, oak-beamed ceiling and a staircase.](/sites/default/files/styles/gallery_thumbnail/public/cottage/2024-05-01/1.mill_cottage_keld_head_farm_in_pickering_lounge_1.jpg?h=861e5b30&itok=p3xZX_Gf)
- 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
- 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.
![](/sites/default/files/styles/gallery_thumbnail/public/cottage/2024-03-15/7.wheelhouse_cottage_keld_head_farm_pickering_north_yorkshire_garden.jpg?h=ba88677a&itok=DVqAkN97)
- 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.
![A heated indoor swimming pool with a hot tub.](/sites/default/files/styles/gallery_thumbnail/public/cottage/789/granary-1.jpg?h=79a786d3&itok=jxaVK7Qc)
- 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.
![Exterior of a long, many-windowed barn conversion to form a single-storey holiday cottage in Pickering.](/sites/default/files/styles/gallery_thumbnail/public/cottage/2024-06-28/1-mallard.pickering-holiday-cottage-exterior_1.jpg?h=82f92a78&itok=WWzQwBRN)
- 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.
![Barn conversions overlook a courtyard with a central flower bed](/sites/default/files/styles/gallery_thumbnail/public/cottage/2024-03-15/1.granary_cottage_keld_head_farm_pickering_north_yorkshire_porch_view.jpg?h=6eb229a4&itok=IHh6CB2D)
- Sleeps
- 4
- Bedrooms
- 2
The Granary is a charming, detached cottage located in the rural area of Keld Head Cottages, near Pickering in Yorkshire. This award-winning farm cottage features an open fire and beautiful exposed beams, creating a warm and cosy ambience. The cottage also offers large, stunning gardens with indoor and outdoor play areas, perfect for a relaxing and enjoyable stay. The beautiful views surrounding the cottage are sure to help you unwind and enjoy a peaceful time away from the hustle and bustle of everyday life.
![2-storey exterior of. stone-built barn conversion overlooking a paved terrace and a lawn](/sites/default/files/styles/gallery_thumbnail/public/cottage/2023-10-16/1.harvest-cottage-pickering-exterior-1.jpeg?h=fbf4b26c&itok=Bgm816qB)
- 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.