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Take a trip on the North Yorkshire Moors Railway from Pickering
Take a trip on the North Yorkshire Moors Railway from Pickering

Self Catering Holiday Cottages in Pickering - Page 2

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54.304240, -0.720684

Relax and unwind at Cowslip Cottage. This charming property is in Levisham, just a two-minute walk from an excellent pub and only six miles from Pickering. There are fantastic footpaths, cycling trails and bridleways in the area, and the owners offer secure bike storage and DIY livery so you can bring your own horse away with you should you wish. The cottage sleeps three people in two bedrooms and can, depending on availability, be booked together with neighbouring Primrose Cottage and the owner's three B&B rooms to accommodate larger groups.

Weekly guide price:
£450 to £650
Short breaks from £100 per night

3  |   2  |   2  |   Yes  |   Yes

Min nights: 3 (off peak) | 7 (peak)

Preferred arrival day: Friday

54.249092, -0.777828

A lovely holiday cottage on the edge of the beautiful North Yorkshire Moors overlooking the steam railway and within easy walking distance of the centre of the market town of Pickering in North Yorkshire. Close to Dalby Forest, Apple Cottage is a great self-catering choice for those who enjoy being active or exploring.

Weekly guide price:
£570 to £800

5  |   3  |   2  |   Yes  |   Yes

Min nights: 7 (off peak) | 7 (peak)

Preferred arrival day: Saturday

54.240995, -0.779283

This spacious holiday cottage is in a quiet location opposite a recreation sports ground, a short walk from the centre of Pickering with its fantastic amenities. It's ideal for couples or families who want to walk, cycle, eat and explore their way around the North York Moors and the Yorkshire Coast. The two-bedroom bungalow sleeps four people and has recently been refurbished and redecorated throughout. There are excellent footpaths from the door and secure bike storage so you can enjoy the region's plentiful opportunities for cycling and mountain biking. 

Weekly guide price:
£425 to £695

4  |   2  |   No  |   Yes  |   Yes

Min nights: Enquire

Preferred arrival day: Friday

54.237426, -0.719914

A delightful holiday cottage in the pretty village of Thornton-le-Dale near Pickering within the North York Moors National Park. With Dalby Forest on the doorstep, Lumley Cottage is a superb self-catering base for exploring the areas many attractions and enjoying a host of outdoor pursuits.

Weekly guide price:
£450 to £895
Short breaks from £100 per night

3  |   2  |   1  |   Yes  |   Yes

Min nights: 3 (off peak) | 7 (peak)

Preferred arrival day: Saturday

54.323364, -0.792029

Stay in luxury at The Hayloft at Flamborough Rigg. Awarded 5 Gold Stars for its consistently high standards, the stone cottage near Pickering in the North York Moors National Park sleeps four people in two bedrooms and is popular with couples and families visiting the area. You can see Cropton Forest from the cottage and garden, and with Dalby Forest also nearby there are an excellent variety of footpaths and cycling trails to enjoy. The Hayloft at Flamborough Rigg is also within easy reach of the Yorkshire Coast, including Whitby and Sandsend. Tourist board rating: 5 Star Gold

Weekly guide price:
£825 to £925
Short breaks from £135 per night

4  |   2  |   2  |   Yes  |   Yes

Min nights: 3 (off peak) | 3 (peak)

Preferred arrival day: Flexible | 5 Star Gold

54.245065, -0.774766

Whether you're a frequent visitor to the North York Moors National Park or seeing it for the first time, you'll find 17 Hallgarth the ideal place to stay. The Grade II listed cottage is comfortable and welcoming and popular with families as well as couples. Pickering offers a great range of amenities and is only 15-minutes from Dalby Forest and Malton (with a mainline train station and excellent foodie scene). York, Whitby and Scarborough are all around half an hour's drive from the cottage making this a great base for exploring the North York Moors National Park.

Weekly guide price:
£410 to £610
Short breaks from £90 per night

4  |   2  |   3+  |   Yes  |   Yes

Min nights: 3 (off peak) | 3 (peak)

Preferred arrival day: Mon/Fri

54.305292, -0.723346

The Horseshoe Cottage is a romantic one-bedroom retreat for two in the heart of Levisham, a pretty village in the North York Moors. With a private garden, log fire, and timeless charm, it’s a welcoming base for couples keen to explore both countryside and coast. Enjoy doorstep access to epic moorland walks, a cracking local pub just moments away, and nearby days out to Whitby, Robin Hood’s Bay, and Dalby Forest. Stylish, snug and seriously scenic—it’s just the spot for a proper Yorkshire escape.

Weekly guide price:
£895 to £1500

2  |   1  |   No  |   No  |   Yes

Min nights: 7 (off peak) | 7 (peak)

Preferred arrival day: Saturday