Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 125 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

  • Sleeps4
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A lovely three-bedroom terraced cottage resting in Pickering, North Yorkshire. Pet-friendly. Near a National Park. Off-road parking. Woodburning stove. Kirkbymoorside 6.7 miles; Helmsley 12.2 miles; Scarborough 18.4 miles. (Ref. 1102719)

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


for 7 nights From €459

  • 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 €646

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Pretty little detached cottage in Stillington village, midway between York and Helmsley. All ground floor with comfortable open plan living. Perfect romantic retreat. York 11 miles. (Ref. 30893)

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


for 7 nights From €524

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Detached modern bungalow, set amidst open farmland near pretty market town of Malton. Comfortable and traditional with cosy woodburning stove. Off road parking, bike storage. Excellent area for moors and coast. Malton 3.5 miles. (Ref. 931402)

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


for 7 nights From €586

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

A pretty cottage nestled in the picturesque village of Rosedale, North Yorkshire. Woodburning stove. Garden. Dishwasher. Kirkbymoorside 7.9 miles; Pickering 10.3 miles. (Ref. 1102061)

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


for 7 nights From €684

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Tourist Board rating

One of our farm based Yorkshire cottages, with lovely views over the moors, 7 miles from the market town of Helmsley. (Ref. 3626)

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


for 7 nights From €394

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From €351

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    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)

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


for 7 nights From €389

Last booked 8 hours ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • 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)

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


for 7 nights From €525

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.0

    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 €680

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From €395

  • 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 €513

  • 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 €506

  • 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 €476

Last booked 8 hours ago
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  • Sleeps9
  • Bedrooms5
  • Pet FriendlyNo

    4.8

    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 €880

  • 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 €666

  • 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 €757

Last booked 7 hours ago
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