Holiday Cottages in Pickering

Within 10 miles
  • Within 1 mile
  • Within 2 miles
  • Within 3 miles
  • Within 5 miles
  • Within 10 miles
  • Within 20 miles
  • Within 30 miles
  • Within 50 miles
1
2
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
Pets
  • Pets
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • Property pet free
7
  • 7
  • 3
  • 4
  • -
  • 1
  • 2
  • 5
  • 6
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
3 Days +/-
  • Exact Dates
  • 1 Day +/-
  • 2 Days +/-
  • 3 Days +/-

British Travel Award Winners!

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

REFINE SEARCH

Your Pickering, North Yorkshire search returned 198 cottages

Relevance (AI)
  • Distance to Location
  • Relevance (AI)
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
Map View
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 £528

See more details
A stone cottage with a tiled roof a blue door with a small porch and white framed windows at Woodside Cottage in Brompton by Sawdon
9
Brompton-by-Sawdon, North Yorkshire, YO13
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Charming semi-detached stone cottage in a peaceful location in the North York Moors National Park, 1.5 miles from Brompton-by-Sawdon. Woodburner, WiFi, off road parking, enclosed front garden. Tastefully furnished to high standard. Scarborough 10 miles. (Ref. 933359)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £373

See more details
A stone building with glass patio doors and a glass balustrade beside a gravel area and wooden fence at Shippon in Beadlam
44
Beadlam, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A romantic, single-storey cottage resting in Beadlam, North Yorkshire. Open-plan. Beautiful views. Helmsley 2.2 miles; Pickering 10.9 miles; York 24.4 miles. (Ref. 1099725)

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

7 nights from £413

See more details
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 £360

See more details
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 £377

See more details
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 £499

See more details
A brick building with multiple doors and windows a tiled roof with solar panels and a lawn in front at Cow Byre in Malton
23
Malton, North Yorkshire, YO17
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stunning ground floor barn conversion five miles from Malton in North Yorkshire. Open-plan living. En-suites. Countryside views. Near North York Moors National Park. (Ref. 943576)

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

7 nights from £532

See more details
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 £379

See more details
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 11th Oct to 18th Oct 2025

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

7 nights from £507

Last booked 7 hours ago
See more details
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 £448

See more details
An outdoor seating area with a table and two chairs next to a small shed and a covered seating area at Bellwether in Helmsley
24
Helmsley, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A superb, shepherd’s hut situated on the outskirts of the market town of Helmsley. Woodburner. WiFi. Rural views. Kirkbymoorside 3.9 miles; Pickering 10.9 miles. (Ref. 986040)

  • Wi-fi
  • Ground floor bedroom

7 nights from £305

See more details
A fenced grassy yard with a white duck in front of a small building at The Brae in Snainton
38
Snainton, North Yorkshire, YO13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A delightful shepherds hut situated in the village of Snainton in Yorkshire. Woodburner. Open-plan accommodation. Views over the Vale of Pickering. Scarborough 10 miles; Pickering 8 miles. (Ref. 961370)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Washing machine

7 nights from £442

See more details
An exterior stone wall with a wooden porch and potted flowers on a gravel ground at The Coach House in Levisham
32
Levisham, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This magnificent stone-built cottage in the beautiful village of Levisham near to the amenities of Pickering. In the North York Moors National Park. Characterful. Private garden. WiFi. Electric car charge point. Pickering 7.2 miles; Scarborough 22 miles. (Ref. 1040743)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher

7 nights from £559

See more details
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 £394

See more details
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

    5.0★

    Perfect

  • 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 £654

See more details
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 £887

Last booked today
See more details
A brick house with a white door and two windows next to a driveway at Glenrae in Thornton-Le-Dale
31
Thornton-Le-Dale, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Glenrae, a charming cottage located in the village of Thornton-Le-Dale in North Yorkshire, short walk to a pub. Pickering 2.5 miles; Scarborough 15.7 miles; York 25.9 miles. (Ref. 1159315)

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

7 nights from £528

See more details
A stone house with solar panels on the roof and a garden with flowers and stone pathway at Thompson Rigg House in Thornton-Le-Dale
43
Thornton-Le-Dale, North York Moors National Park, YO13
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Thompson Rig House is a cottage in Langdale End near Scarborough, North Yorkshire, boasting a woodburning stove, underfloor heating, and hot tub. Pickering 15.4 miles; Whitby 22.9 miles; York 38.7 miles. (Ref. 1164248)

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

7 nights from £892

See more details
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 £363

See more details
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 £407

Last booked 2 days ago
See more details
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.