Holiday Cottages in Pickering

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We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Holiday Cottages in Pickering

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Your Pickering, North Yorkshire search returned 197 cottages

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Map View
A red front door with windows on either side on a stone cottage called Castle Cottage at 12 Castlegate in Pickering
34
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stone, terraced cottage resting in market town of Pickering, North Yorkshire. Open fire. WiFi. Excellent area for walking, cycling and touring. Close to coast. Kirkbymoorside 7 miles. (Ref. 1119779)

  • Wi-fi
  • Dishwasher

7 nights from €418

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A brick house with a tiled roof a black door and several windows behind a black metal fence at Derwent House in Pickering
30
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This pretty, two-bedroom holiday home rests in Pickering, North Yorkshire. Near a National Park. Enclosed garden. Smart TV. Off-road parking. Kirkbymoorside 7.8 miles; Helmsley 13.4 miles; Scarborough 18.3 miles; Whitby 20.5 miles; York 26.3 miles. (Ref. 1017413)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from €595

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A stone building with white windows and doors and a covered archway at Dove Cottage in Pickering
16
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Grade II listed mid-terrace cottage resting in Pickering town centre. Woodburning stove. Pet-friendly. Kirkbymoorside 7.2 miles; Scarborough 17.9 miles. (Ref. 1033746)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €522

Last booked yesterday
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A dining area with a wooden table and chairs beside a living room with sofas a tv and a window seat at Potter Hill Cottage in Pickering
25
Pickering, North Yorkshire, YO18
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

This inviting mid-terrace sits at the centre of Pickering in North Yorkshire, on the fringes of the North York Moors National Park. Three-storey. Pet-friendly. Amenities in walking distance. Malton 8.7 miles; Scarborough 18.2 miles; York 26.8 miles. (Ref. 1025071)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €438

Last booked yesterday
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An outdoor seating area with white metal benches and chairs next to stone wall with black door and potted plants at Brookwood in Thornton Dale
29
Thornton Dale, North York Moors National Park, YO18
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

An opulent three-bedroom property resting in Thornton Dale, North Yorkshire. Garden. Off-road parking. Close to North York Moors National Park. North Riding Forest Park 5.7 miles; Scarborough 15.5 miles; The Bay Beach 23.3 miles. (Ref. 1132285)

  • Wi-fi
  • Off-road parking

7 nights from €703

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A stone house exterior with white framed windows and hanging flower baskets at Beckdale in Thornton-Le-Dale
48
Thornton-Le-Dale, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stunning, two-bedroom cottage resting in Thornton-le-Dale, North Yorkshire. In the North York Moors National Park. Private Garden. Off-road parking. Pickering 2.6 miles; Scarborough 15.5 miles; York 26.6 miles. (Ref. 1097167)

  • Wi-fi
  • Off-road parking

7 nights from €579

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A row of brick and stone houses with tiled roofs and multiple doors and windows along a roadside at Duckys in Pickering
35
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely three-bedroom terraced cottage resting in Pickering, North Yorkshire. Pet-friendly. Near a National Park. Off-road parking. Woodburning stove. Kirkbymoorside 6.7 miles; Helmsley 12.2 miles; Scarborough 18.4 miles. (Ref. 1102719)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €529

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A stone cottage with wooden windows and doors next to a garden gate at The Cottage in Thornton Dale
19
Thornton Dale, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A picturesque semi-detached cottage in the popular village of Thornton Dale in North Yorkshire. Pickering 3 miles. Scarborough 16 miles. (Ref. 1005042)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €457

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Stone exterior of a cottage with a red door four white windows and flower pots at Barn Cottage Marton near Kirkbymoorside
25
Marton near Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

An attractive, mid-terrace barn conversion resting in Marton near Kirkbymoorside, North Yorkshire. Woodburning stove. Pet-friendly. Enclosed garden. Off-road parking. Pickering 4.8 miles; Helmsley 9.1 miles. (Ref. 1081033)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €440

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A stone cottage with two doors and two windows next to a grassy area with trees at Beck Cottage in Pickering
18
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Attractive character cottage, opposite steam railway in Pickering. Beams, stripped pine doors, high quality accommodation. Town centre 10 mins walk. (Ref. 24339)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

  • 10% off - Sat 4th Oct to 11th Oct 2025

  • 10% off - Sat 18th Oct to 25th Oct 2025

7 nights from €588

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An outdoor garden with a lodge and seating at Ryedale Country Lodges - Willow Lodge in Kirkbymoorside
23
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A wood-clad lodge resting within the town of Kirkbymoorside. All-ground-floor. Pet-friendly. WiFi. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011653)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from €556

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Stone cottages with gray doors and white framed windows along a street at The Old Cartway in Pickering
19
Pickering, North Yorkshire, YO18
  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A grade II listed mid-terrace stone cottage set in the pleasant town of Pickering in North Yorkshire. Ramp access from the rear garden. Short distance to town centre. (Ref. 964829)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €777

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A log cabin with patio furniture and lawn at Ryedale Country Lodges - Hazel Lodge Kirkbymoorside
29
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A superb, detached lodge resting on the outskirts of Kirkbymoorside. All-ground-floor. WiFi. Pet-friendly. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011649)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from €607

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A brick house with a tiled roof and multiple windows surrounded by potted plants and flowers at Runswick in Pickering
25
Pickering, North Yorkshire, YO62
  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

This delightful detached house is situated in Sinnington, North Yorkshire. WiFi, Pet-friendly, Off-road parking. Pickering 3 miles; Kirkbymoorside 3.5 miles. (Ref. 998951)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from €693

Last booked yesterday
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A gated entrance with wooden houses and a large barn in the background at Eagles Peak in Allerton near Thornton-Le-Dale
40
Allerton near Thornton-Le-Dale, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A stunning two bedroom lodge nestled in Allerston, North Yorkshire. Hot tub. Woodburning stove.Off-road parking. Rural. Pickering 5.2 miles; Scarborough 16.2 miles; Helmsley 17.8 miles. (Ref. 1097488)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Baby-friendly

7 nights from €1027

Last booked 9 hours ago
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A brick house with a tiled roof and blue doors behind a brick wall at Bellafax Cottage in Marishes near Pickering
20
Marishes near Pickering, North Yorkshire, YO17
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Attractive, detached red brick traditional cottage on owner's farm, between Pickering and Thornton-le-Dale. Open fire, bike storage, views over open countryside. Good walking/cycling country. Pickering 3 miles. (Ref. 921426)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from €378

Last booked yesterday
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Exterior of a stone building with two green wooden doors and a window under a tiled roof at Puddleduck Cottage in Thornton-Le-Dale
19
Thornton-Le-Dale, North York Moors National Park, YO18
  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A charming, two-bedroom, stone-fronted cottage resting in Thornton-le-Dale, North Yorkshire. Characterful. Close to amenities. In National Park. Ground-floor accommodation. Pickering 2.8 miles; Scarborough 15.6 miles; York 25.4 miles. (Ref. 1128348)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from €472

Last booked 2 days ago
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A front yard with a driveway garage lawn flowers and two brick houses at Field Cottage in Kirkbymoorside
25
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A lovely, two-bedroom cottage resting in Kirkbymoorside, North Yorkshire. Near National Park. Countryside views. Close to amenities. Contemporary. Ground-floor living. Enclosed garden. Helmsley 6.1 miles; Pickering 7.6 miles. (Ref. 1131837)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from €421

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Two modern grey cabins with large glass windows and outdoor seating surrounded by a gravel and mulch garden at Foxes Den in Allerston near Thornton Dale
44
Allerston near Thornton Dale, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stunning, two-bedroom lodge resting in Allerston near Thornton Dale, North Yorkshire. Hot tub. Woodburning stove. Open-plan. Pickering 5.2 miles; Scarborough 16.2 miles; Helmsley 17.8 miles. (Ref. 1097485)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher

7 nights from €998

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A garden with wooden table and chairs and plants in front of a stone house with large windows at The Granary in Appleton-le-Moors
19
Appleton-le-Moors, North York Moors & Coast, YO62
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Delightful detached stone cottage on owner's complex in Appleton-le-Moors village. Cosy, characterful accommodation with open fire, garden room, fine views over open countryside. Wonderful walking/cycling from the door. Kirkbymoorside 3.5 miles. (Ref. 936454)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from €520

Last booked yesterday
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Map View

Holiday cottages in Pickering offer a superb location for exploring all that the North York Moors has to offer! An ancient market town nestled between York and Scarborough, Pickering is the ideal base to explore the wealth of attractions in North Yorkshire.

Take a look at this collection today and find the right Pickering cottage for you today!

Why Pickering Cottages?

Staying in a holiday cottage in Pickering offers access to the stunning countryside as well as an array of nearby towns and exciting attractions.

Choose from a diverse selection of holiday cottages in Pickering, from quaint stone-built bolt holes to impressive, converted farmhouses. No matter your tastes or interests, the area surrounding self-catering Pickering properties is sure to impress.

Pickering is steeped in history, with highlights like Pickering Castle, a well-preserved Norman fortress. The town has a number of stores and independent shops along with pubs and eateries, so you have everything you could possibly need for your break away.

So, whether you're seeking outdoor adventure or just a peaceful escape, these Pickering cottages offer a fantastic base to experience it all.

Places to Visit near Holiday Cottages in Pickering

Staying in a holiday cottage in Pickering places you in the perfect location to explore some of North Yorkshire’s most captivating destinations.

Close by is the North Yorkshire Moors Railway, where you can take a nostalgic steam train journey through breathtaking countryside, stop at charming villages like Goathland, famous as the setting for Heartbeat and Harry Potter’s Hogsmeade Station.

Other family-friendly attractions close by are like Flamingo Land Resort, which combines a theme park and zoo, perfect for young families and Dalby Forest which offers miles of walking and cycling trails, as well as a Go Ape adventure course for thrill-seekers.

Looking for more outdoor adventures from your Pickering cottage? Then you can enjoy the wild beauty of the North York Moors National Park, with fantastic landscapes and a wide range of stunning walks and trails; it is a must-visit for those looking to step back into nature.

For a coastal escape, visit the nearby town of Whitby, known for its historic abbey, picturesque harbour, and even connections to Dracula; it is certainly worth a visit. Also, look out for some fantastic fish and chip shops where you can enjoy a classic seaside meal.

With so much to see and do, holiday cottages in Pickering make for a fantastic base for discovering the best of North Yorkshire.

Other Destinations near Holiday Cottages in Pickering:

Ampleforth

Filey

Kirkbymoorside

Malton

Ruswarp

Scarborough

Sleights

Thirsk

York

Types of Pickering Holidays

If you still haven’t found what you’re looking for, view the full collection of cottages in the North York Moors! You can also choose from these wonderful lodges in Pickering as well as these dog-friendly holiday cottages in Pickering.