Holiday Cottages in Pickering

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Your Pickering, North Yorkshire search returned 196 cottages

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  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.8

    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 £456

  • Sleeps4
  • Bedrooms3
  • PetsNo

    4.7

    Sykes Rating

A charming cottage situated in Lockton near Pickering, North Yorkshire. Off-road parking. Woodburning stove. Enclosed garden. Pickering 5.8 miles; Scarborough 20.3 miles. (Ref. 1105052)

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

7 nights from £384

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

A characterful barn conversion resting on a working farm near the town of Kirkbymoorside. TV with Freeview. Countryside views. Near North York Moors National Park. Dog-friendly. (Ref. 974385)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from £320

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

This enchanting holiday home rests in Allerston near to the amenities of Thornton-Le-Dale, North Yorkshire. Electric fire. Pet-friendly. WiFi. Near to the North York Moor National Park. Thornton-le-Dale 3.1 miles; Scarborough 13.3 miles. (Ref. 1053249)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 15% off - Fri 22nd Aug to 29th Aug 2025

7 nights from £392

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

This romantic detached bungalow resides on the outskirts of Pickering, North Yorkshire. WiFi. Remote. Garden. Woodburning stove. Kirkbymoorside 7.5 miles; Helmsley 13 miles; Scarborough 18.5 miles. (Ref. 1062267)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from £372

Last booked yesterday
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7 nights from £397

7 nights from £395

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

This quaint, single-storey barn conversion rests in Scagglethorpe, North Yorkshire. Pet-friendly. Off-road parking. Woodburning stove. Garden with furniture. Malton 4.3 miles; Scarborough 18.9 miles; York 22.5 miles. (Ref. 981428)

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

7 nights from £317

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

Superb single-storey barn conversion in courtyard setting. High quality furnishings, spacious sitting room, romantic pretty double bedroom. Ideal for coast and exploring North York Moors. Scarborough 7 miles. (Ref. 911892)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom

7 nights from £420

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

A lovely terraced cottage in Pickering with a private enclosed garden. Pet-friendly. Woodburner. Ceiling beams. Ideal for visiting North York Moors railway located in the town. Kirkbymoorside 7 miles. (Ref. 953578)

  • Wi-fi
  • Washing machine

7 nights from £396

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Sykes Rating

Midsummer Cottage, a delightful holiday cottage resting in Marishes near Thornton Dale, North Yorkshire. Single-storey. Open-plan. Enclosed garden. Pickering 5.1 miles; Helmsley 17.9 miles; Scarborough 18.1 miles. (Ref. 1156276)

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

7 nights from £376

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

Nell's Cottage is a wonderful, single-storey cottage nestled in rural East Knapton, near Rillington, North Yorkshire. Pet-friendly. Open-plan. Romantic. Malton 8 miles; North York Moors National Park 13.2 miles; York 25.6 miles; Scarborough 15.4 miles. (Ref. 1148580)

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

7 nights from £491

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

Bumblebee Glamping Pod, a fabulous, single-storey lodge, is positioned in Marishes near Thornton Dale in North Yorkshire, enjoying a bubbling hot tub. Pickering 5.1 miles; Helmsley 17.9 miles; Scarborough 18.1 miles. (Ref. 1163430)

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

7 nights from £461

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

Millers Cottage is a detached bungalow resting in the hamlet of Old Malton, near Malton, North Yorkshire. Close to a shop and pub. Couple’s retreat. Malton 1 mile; Pickering 7.4 miles; North York Moors National Park 9.4 miles. (Ref. 1147474)

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

7 nights from £377

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

Beautiful stone cottage in the North York Moors National Park, close to the village of Hutton-le-Hole. Exposed beams. Surrounded by countryside. Hutton-le-Hole 1.5 miles. (Ref. 975266)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £343

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

This attractive single-storey property rests in Malton, North Yorkshire. Near a National Park. Pet-friendly. Ground-floor accommodation. Hot tub. Scarborough 18.5 miles; York 21.9 miles. (Ref. 1121314)

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

7 nights from £737

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

A delightful, one-bedroom home resting in Sawdon near East Ayton, North Yorkshire. Near National Park. Contemporary. Romantic. Private patio. Rural views. Scarborough 10 miles; North York Moors National Park 13.1 miles; Flamborough 24.3 miles. (Ref. 1100343)

  • Wi-fi
  • Off-road parking

7 nights from £389

Last booked yesterday
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7 nights from £388

Last booked 2 hours ago
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  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A charming two-bedroom cottage resting near Brompton-By-Sawdon, Scarborough. Woodburning stove. Close to amenities. Pet-friendly. Beautiful views. Scarborough 9.8 miles; Pickering 9.9 miles; York 32.3 miles. (Ref. 1108141)

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

7 nights from £384

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Delightful conversion of old cow byre in centre of Wrelton. Exposed timbers, wooden floors. Quality cottage, very high standard. Excellent walking and touring base. Pickering 3 miles. (Ref. 1577)

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

7 nights from £311

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 North Yorkshire Holidays


Secure your next break in the Yorkshire countryside today with a holiday cottage in Pickering!

If you are thinking about taking your pet with you on your adventure, then see this selection of dog-friendly properties in the North York Moors.

Looking for something different? Then why not view this collection of log cabins in North Yorkshire, glamping pods in North Yorkshire and glamping pods with hot tubs in North Yorkshire.

For other options with a hot tub, browse this selection of North Yorkshire cottages with hot tubs.

if you are looking for a quick getaway, see this selection of short breaks in North Yorkshire and last-minute cottages in North Yorkshire. Why not try a break in a holiday park too with these wonderful holiday parks in North Yorkshire.

If you still haven’t found what you’re looking for, view the full collection of holiday cottages in North Yorkshire and cottages in the North York Moors!