Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 120 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps6
  • Bedrooms4
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A grade II listed mid-terrace stone cottage set in the pleasant town of Pickering in North Yorkshire. Ramp access from the rear garden. Short distance to town centre. (Ref. 964829)

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


for 7 nights From £670

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A welcoming, detached lodge resting in Cropton near Middleton, North Yorkshire. Ground-floor living. Pet-friendly. Off-road parking. Aislaby 2.8 miles; Pickering 5.2 miles; York 30.6 miles. (Ref. 1003270)

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


for 7 nights From £582

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Damson Croft is a charming bungalow in Lastingham within the North York Moors National Park, boasting a one-acre garden, barbecue, and countryside views. 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 From £434

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Chapel Cottage is a characterful, Grade II listed cottage in Stillington, North Yorkshire, with exposed beams, an open fire, and an enclosed courtyard. York 10 miles. (Ref. 28836)

  • Pets go free
  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights From £439

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £407

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights From £537

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Delightful stone cottage in courtyard, set in open countryside. Character, quality accommodation. Oak floors, exposed beams. Kirkbymoorside 1.5 miles, Pickering 6 miles. (Ref. 929319)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £579

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly


for 7 nights From £404

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    3.2

  • 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)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher


for 7 nights From £431

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £652

  • Sleeps9
  • Bedrooms5
  • Pet FriendlyNo

    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 From £794


for 7 nights From £981