Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 150 cottages

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An outdoor patio area with a round table and six chairs under a white umbrella beside a brick wall at Beaver Cottage in Little Thirkleby near Thirsk
35
Little Thirkleby near Thirsk, North Yorkshire, YO7
  • Sleeps6
  • Bedrooms3
  • PetsNo

  • Sykes rating

Beaver Cottage is located in the village of Little Thirkleby near Thirsk, North Yorkshire with an open-plan living space and access to an indoor heated pool on site. Northallerton 13.3 miles; North York Moors National Park 3.4 miles; York 21 miles. (Ref. 1173736)

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


for 7 nights $1242

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A stone cottage with a tiled roof and a small garden with flowers at Croft Head Cottage in Wrelton near Pickering
8
Wrelton near Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Grade II listed, semi-detached, former coaching inn, near centre of Wrelton village. Full of character, exposed beams and woodburning stove. Pickering 3 miles. (Ref. 1844)

  • Wi-fi
  • Washing machine


for 7 nights $401

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A stone house with a tiled roof and daffodils in a garden at The Arches in Farndale near Kirkbymoorside and Helmsley
39
Farndale near Kirkbymoorside and Helmsley, North York Moors National Park, YO62
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Magnificent semi-detached barn conversion in Farndale. Full of character and charm, exposed beams and open fire. Excellent walking from the doorstep. Kirkbymoorside 10 miles. (Ref. 1391)

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


for 7 nights $590

Last booked yesterday
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A wooden cabin with outdoor seating and a covered hot tub on a stone patio at Westfield Lodge in Terrington near Sheriff Hutton
18
Terrington near Sheriff Hutton, North Yorkshire, YO60
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Westfield Lodge is a charming, detached, single-storey lodge in Terrington, North Yorkshire, boasting off-road parking, a hot tub, and an electric fire. Malton 9.2 miles; York 13.4 miles. (Ref. 1095905)

  • Wi-fi
  • Ground floor bedroom
  • Hot Tub


for 7 nights $660

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A stone house with a tiled roof a wooden bench and potted plants on a gravel path with a grassy lawn in front at The Burrows in Wass near Helmsley
24
Wass near Helmsley, North York Moors National Park, YO61
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Burrows, a charming holiday cottage located in the quaint town of Helmsley, North Yorkshire. Woodburning stove. Enclosed garden. In North York Moors.Helmsley 6.4 miles; York 21.3 miles; Scarborough 38 miles. (Ref. 1150998)

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


for 7 nights $680

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Row of brick terraced houses with different colored front doors along a street with grass verge at Cloverleaf Cottage in Pickering
18
Pickering, North Yorkshire, YO18
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A delightful mid-terrace cottage resting within the market town of Pickering. Woodburning fire. Fibre Optic WiFi. Pub within 0.2 miles. Scarborough 18 miles; Whitby 22 miles. (Ref. 1003948)

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


for 7 nights $605

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A row of brick houses with arched windows and doors with potted plants outside at Chapel Cottage in Stillington near Easingwold and York
33
Stillington near Easingwold and York, North Yorkshire, YO61
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Attractive, period cottage in pretty Stillington village. Character beams, open fire, enclosed sunny courtyard garden. Quality accommodation, well-equipped and comfortable. Many attractions close by. York 10 miles. (Ref. 28836)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $590

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An outdoor stone stairway with wooden railings leading to a stone building with tiled roof and small windows at The Old Cart House in Farndale near Kirkbymoorside and Helmsley
39
Farndale near Kirkbymoorside and Helmsley, North York Moors National Park, YO62
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Delightful semi-detached barn conversion in Farndale, 2 miles from Low Mills. Fabulous farmhouse kitchen with open fire. Excellent walking and cycling nearby. Kirkbymoorside 10 miles. (Ref. 1392)

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


for 7 nights $719

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A stone cottage with white framed windows and doors and a tiled roof at Lockton Cottage in Pickering
9
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Beautifully presented stone cottage just outside Pickering. Cosy and characterful, beams, open fire. Off road parking, pleasant lawned rear garden. Pickering 1 mile. (Ref. 983666)

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


for 7 nights $479

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A stone cottage with red tiled roof green door and four windows with plants in front at Harwood Cottage in Hovingham
30
Hovingham, North Yorkshire, YO62
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4★

    Good

  • Sykes rating

Harwood Cottage, a stunningly-presented holiday home in the charming village of Hovingham. Streamside. Garden with barbecue. Conservatory. Child-friendly. Helmsley 7.9 miles; Malton 8.2 miles; York 17.3 miles. (Ref. 1155772)

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


for 7 nights $696

Last booked yesterday
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Honeysuckle Cottage - 1174608 - photo 1
28
Oswaldkirk near Helmsley, North Yorkshire, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Honeysuckle Cottage is a holiday cottage situated in the pleasant little village of Oswaldkirk near Helmsley in North Yorkshire, with a woodburning stove. Kirkbymoorside 9.9 miles; Thirsk 14.7 miles; Pickering 16.8 miles; York 20.8 miles. (Ref. 1174608)

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

  • 5% off - Thu 23rd Oct to 31st Dec 2025


for 7 nights $579

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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 $741

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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 $547

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Stone exterior of a two-story house with white windows a small green door and potted plants in front at Westgate Cottage in Pickering
18
Pickering, North Yorkshire, YO18
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

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

A delightful semi-detached, stone-built cottage in the popular market town of Pickering, North Yorkshire. WiFi. Gardens with furniture. Great base for walking. (Ref. 904079)

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


for 7 nights $461

Last booked 2 days ago
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A stone house with multiple windows a green door a gravel driveway and a fenced garden at 2 Primrose Villas in Rosedale Abbey
35
Rosedale Abbey, North York Moors & Coast, YO18
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A charming semi-detached stone cottage, resting in Rosedale Abbey, within the North York Moors National Park. Woodburning stove. Off-road parking. Kirkbymoorside 7.2 miles; Pickering 11.6 miles; 17.6 miles. (Ref. 1034768)

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


for 7 nights $539

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A small dark wooden house with plants and flowers around the entrance and a large grassy garden with trees and shrubs at Damson Croft in Lastingham
21
Lastingham, North York Moors National Park, YO62
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A charming single-storey cottage resting in the pretty village of Lastingham, North Yorkshire. Barbecue. In North York Moors National Park. Countryside views. Single-storey. Kirbymoorside 5 miles; Pickering 4.9 miles; York 31.5 miles (Ref. 14454)

  • Wi-fi
  • Electric vehicle charging
  • Ground floor bedroom
  • Baby-friendly


for 7 nights $532

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A stone cottage with a blue door and parking area at The Annex in York
16
Helmsley, North Yorkshire, YO62
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Walnut Cottage is a romantic retreat near Helmsley, North Yorkshire, boasting proximity to North York Moors National Park and countryside views from the garden. Kirkbymoorside 4.4 miles; Pickering 11.3 miles; Thirsk 17.7 miles; York 24.5 miles. (Ref. 1174223)

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

  • 5% off - Thu 16th Oct to 22nd Dec 2025


for 7 nights $482

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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

    4.9★

    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 $452

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A garden with outdoor wooden table and chairs surrounded by bushes and trees at Badger in Little Thirkleby near Thirsk
23
Little Thirkleby near Thirsk, North Yorkshire, YO7
  • Sleeps6
  • Bedrooms3
  • PetsNo

  • Sykes rating

Badger is an elegant house in Little Thirkleby, North Yorkshire, boasting an enclosed garden, and access to a tennis court, swimming pool. Ripon 15.5 miles; Helmsley 12.2 miles; York 21 miles. (Ref. 1170004)

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


for 7 nights $1249

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Angram Cottage - 1172363 - photo 1
19
Angram Grange near Thirsk, North Yorkshire, YO7
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Angram Cottage is a gorgeous abode set in the countryside of Angram Grange near Thirsk, North Yorkshire, near the pretty North York Moors National Park. North York Moors National Park 6.1 miles; Northallerton 15.1 miles; York 20.2 miles. (Ref. 1172363)

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


for 7 nights $661

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