Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 119 cottages

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  • 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 £396

  • 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 £439

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Sixpence Cottage is a homely cottage in the town of Pickering, North Yorkshire, boasting a woodburning stove, and dishwasher, with nearby pubs and shops. Kirkbymoorside 6.9 miles; Helmsley 12.4 miles; Scarborough 18.2 miles; Whitby 21.1 miles; York 26.2 m (Ref. 1084507)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • 10% off - Mon 13th Apr to 31st May 2026


for 7 nights £468

  • 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

  • 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

  • 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 6 hours ago
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  • 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

  • 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

  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

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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

  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.0

  • Sykes rating

St Gregory’s Cottage is a lovely, pet-friendly, single-storey cottage located in the village of Oswaldkirk, North Yorkshire, boasting a woodburning stove. Kirkbymoorside 10 miles; Thirsk 14.3 miles; Pickering 16.8 miles; York 23.9 miles. (Ref. 1174134)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights £383

  • Sleeps4
  • Bedrooms2
  • PetsYes

    3.6

    Good

  • Sykes rating

A traditional cottage resting on a farm in Fadmoor, North Yorkshire. Woodburning stove. Character features. Dishwasher. Kirkbymoorside 2.8 miles; Helmsley 7.8 miles; Pickering 10.3 miles. (Ref. 1123586)

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


for 7 nights £418


for 7 nights £981