Holiday Cottages in Pickering

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Your Pickering, North Yorkshire search returned 170 cottages

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An outdoor entrance area with steps and potted plants between brick pillars at Chalet 1 in Sherburn
Offer
23
Sherburn, North Yorkshire, YO17
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.4★

    Good

  • Sykes rating

An attractive, single-storey, studio-style chalet resting in East Heslerton near Sherburn, North Yorkshire. Hot tub. Allocated parking. Decking with furniture. Pet-free. Smart TV. Filey 12.6 miles; Scarborough 12.8 miles; York 38.1 miles. (Ref. 1093029)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub

  • 15% off - Fri 10th Apr to 28th May 2026


for 7 nights £340

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An outdoor patio with a table and chairs and a closed umbrella in front of a stone house with tiled roof at Brewers Cottage in Pickering
21
Pickering, North York Moors & Coast, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.9★

    Good

  • Sykes rating

Brewers Cottage is a delightful cottage with a toasty woodburning stove and accepting pets, resting in the village of Cropton in North Yorkshire. Aislaby 2.5 miles; Pickering 5 miles; York 30.6 miles. (Ref. 1162947)

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


for 7 nights £404

Last booked yesterday
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A small stone cottage with a green door and window surrounded by paved ground and a garden at Peg's Cottage in Pockley near Helmsley
16
Pockley near Helmsley, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Pretty, detached, ground floor stone cottage in a small hamlet near Helmsley. Cosy, characterful accommodation for couples. WiFi. Pretty garden. Superb walking country. Helmsley 2 miles. (Ref. 917006)

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


for 7 nights £330

Last booked yesterday
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Exterior view of Cowshed Cottage in East Knapton near Rillington
33
East Knapton near Rillington, North Yorkshire, YO17
  • Sleeps2
  • Bedrooms1
  • PetsYes

  • Sykes rating

Cowshed Cottage is a barn conversion in East Knapton, North Yorkshire, offering a romantic, pet-friendly escape with fantastic countryside views. Malton 8 miles; Scarborough 16 miles; Bridlington 21.7 miles. (Ref. 1183456)

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


for 7 nights £351

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A stone cottage with potted plants outside on a gravel path at Adelaides Cottage in Pickering
20
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.0★

    Good

  • Sykes rating

A charming two-bedroom cottage resting in Pickering, North Yorkshire. Near North York Moors National Park. Original features. Close to amenities. Kirkbymoorside 7.2 miles; Helmsley 12.7 miles; Scarborough 18 miles; Whitby 20.8 miles. (Ref. 1111683)

  • Wi-fi
  • Dishwasher


for 7 nights £490

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A stone house with a tree and streetlamp in front at Cobbler's Cottage in Pickering
20
Pickering, North Yorkshire, YO18
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

Lovely semi-detached stone cottage in central Pickering. Oak flooring, comfortable family accommodation. Ideal location for moors and coast. Scarborough 18 miles. (Ref. 936135)

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


for 7 nights £582

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Stone terrace house with blue door and windows with white frames at Hogwarts Cottage in Pickering
15
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Charming mid-terraced cottage, opposite steam railway in Pickering. Cosy, comfortable accommodation. Excellent area for walking, cycling and touring. Kirkbymoorside 7 miles. (Ref. 927236)

  • Wi-fi
  • Washing machine


for 7 nights £306

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A brick cottage with a white door and chairs on a patio in front of a garden at Ghyll Cottage in Rosedale Abbey
17
Rosedale Abbey, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Pretty terraced cottage in sleepy hamlet on edge of Rosedale Abbey. Cosy, characterful accommodation with woodburning stove and wonderful views over countryside. Superb walks from the door. Kirkbymoorside 7 miles. (Ref. 27834)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £333

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An entrance with steps leading to a door flanked by brick pillars and potted plants at Chalet 2 East Heslerton near Sherburn
Offer
23
East Heslerton near Sherburn, North Yorkshire, YO17
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2★

    Good

  • Sykes rating

A stylish, studio-style chalet resting in East Heslerton near Sherburn, North Yorkshire. Smart TV. Hot tub. Pet-free. Filey 12.6 miles; Scarborough 12.8 miles; York 38.1 miles. (Ref. 1094315)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub

  • 15% off - Fri 10th Apr to 28th May 2026


for 7 nights £370

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Brookleigh - 22745 - photo 1
33
Hutton-le-Hole, North York Moors National Park, YO62
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.2★

    Good

  • Sykes rating

Charming, stone, period cottage in pretty village of Hutton-le-Hole. Open fire, cosy, comfortable accommodation. Private rear garden, lovely views over village green. Walkers' delight. Kirkbymoorside 3.5 miles. (Ref. 22745)

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


for 7 nights £407

Last booked 4 hours ago
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Yellow daffodils growing next to a stone wall and wooden door outside a building with a tiled roof at The Old Coach House in Thornton-Le-Dale
35
Thornton-Le-Dale, North York Moors National Park, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3★

    Good

  • Sykes rating

A sympathetically-converted, two-bedroom barn resting in Thornton-Le-Dale, North Yorkshire. In National Park. Original features. Close to amenities. Family-friendly. Ground-floor living. Pickering 3 miles; Scarborough 15.1 miles; York 26.2 miles. (Ref. 1126664)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 7 nights £454

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A stone facade of a residential building with multiple windows and two front doors
27
Rosedale Abbey, North York Moors National Park, YO18
  • Sleeps9
  • Bedrooms5
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

The Old Post Office is a charming five-bedroom house in Rosedale Abbey, in the heart of the North York Moors National Park. WiFi, Dishwasher, Washing machine, Baby-friendly. Kirkbymoorside 7.9 miles; Pickering 10 miles; Whitby 16.6 miles. (Ref. 1166944)

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


for 7 nights £799

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An outdoor view of a house with garden and gravel pathway at Low Muffles Bridge
24
Hartoft near Rosedale Abbey, North York Moors National Park, YO18
  • Sleeps5
  • Bedrooms2
  • PetsNo

  • Sykes rating

Low Muffles Bridge is a comfy, peaceful cottage in a dark skies area of North Yorkshire, with lovely views and trails on all sides. Whitby 20.7 miles; Scarborough 26.2 miles; York 34.2 miles. (Ref. 1176206)

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


for 7 nights £402

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A stone cottage with blue window frames and a wooden picnic table in a gravel courtyard at Foxglove Cottage in Harome
11
Harome, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.9★

    Good

  • Sykes rating

A snug ground-floor cottage tucked away in the quiet village of Harome near Beadlam in North Yorkshire. Electric fire. Romantic retreat. Helmsley 2.7 miles; Pickering 12.3 miles; York 22.5 miles. (Ref. 1069744)

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


for 7 nights £562

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An outdoor area with wooden chairs a wooden shepherds hut and trees at The Hideaway Shepherd's Hut in Langdale End near Thornton-Le-Dale
23
Langdale End near Thornton-Le-Dale, North York Moors National Park, YO13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A rustic shepherd's hut resting in a rural location in the quaint village of Langdale End, near Thornton-le Dale, North Yorkshire. Private parking. Romantic. Woodburning stove. Fire pit. Pickering 11.1 miles; Scarborough 12.5 miles; York 34.6 miles. (Ref. 1128614)

  • Off-road parking
  • Ground floor bedroom


for 7 nights £363

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Two empty champagne flutes and a bottle of champagne on the edge of a bubbling hot tub at Chalet 4 East Heslerton near Sherburn
Offer
22
East Heslerton near Sherburn, North Yorkshire, YO17
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.1★

    Good

  • Sykes rating

This lovely, single-storey, studio-style chalet rests in East Heslerton near Sherburn, North Yorkshire. Pet-free. Smart TV. Hot tub. Allocated parking. Decking with furniture. Filey 12.6 miles; Scarborough 12.8 miles; York 38.1 miles. (Ref. 1094317)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub

  • 15% off - Fri 10th Apr to 28th May 2026


for 7 nights £340

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An outdoor hot tub with bubbling water next to two chairs and a table on a patio at Chalet 5 in Sherburn
Offer
19
Sherburn, North Yorkshire, YO17
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2★

    Good

  • Tourist Board rating

This compact, single-storey, studio-style chalet rests in East Heslerton near Sherburn, North Yorkshire. Allocated parking. Hot tub. Pet-free. Smart TV. Decking with furniture. Filey 12.6 miles; Scarborough 12.8 miles; York 38.1 miles. (Ref. 1094318)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub

  • 15% off - Fri 10th Apr to 28th May 2026


for 7 nights £370

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A stone cottage with a tiled roof and white doors with a black bench outside and a car parked on a driveway at Small Cottage in Fadmoor
14
Fadmoor, North York Moors National Park, YO62
  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.8★

    Good

  • Sykes rating

A cute, one-bedroom farm cottage resting in Fadmoor, North Yorkshire. Open-plan living. Romantic. Shared garden. Kirkbymoorside 2.8 miles; Helmsley 7.8 miles; Pickering 10.3 miles. (Ref. 1123588)

  • Wi-fi


for 7 nights £353

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Exterior view of a row of brick and stone houses with windows and doors on a street at Howe End Cottage in Kirkbymoorside
21
Kirkbymoorside, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Cosy town house in heart of Kirkbymoorside. Three storeys, welcoming accommodation. Convenient location, good base for moors, coast, York and more. (Ref. 17787)

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


for 7 nights £653

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A brick house with a wooden pergola and hot tub in a gravel yard at Fox Retreat in Sherburn
25

Holiday Park

Sherburn, North Yorkshire, YO17
  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Fox Retreat, a delightful holiday bungalow nestled just outside Sherburn, North Yorkshire. Single-storey. Hot tub. Enclosed garden. Private parking. Filey 12.1 miles; Scarborough 12.3 miles; York 28.5 miles. (Ref. 1153179)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub


for 7 nights £634

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