Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 119 cottages

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  • 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 £502

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A delightful cottage located in the village of Pickering in North Yorkshire. Open fire. Breakfast bar. Exposed beams. Fibre Optic WiFi. Kirkbymoorside 7 miles; Helmsley 13 miles. (Ref. 969686)

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


for 7 nights £475

  • Sleeps4
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights £392

Last booked 2 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A gorgeous, one-bed hut sitting in a rural location in Chop Gate, near Stokesley, North Yorkshire. Countryside location. Ideal for couples. Rural views. Great Ayton 10.4 miles; Saltburn-by-the-Sea 20.2 miles. (Ref. 1126877)

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


for 7 nights £515

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A spacious annexe cottage in the village of Hushtwaite in North Yorkshire. Open-plan living. En-suite. York 13 miles. (Ref. 959719)

  • Wi-fi
  • Off-road parking
  • Games room


for 7 nights £309

  • Sleeps6
  • Bedrooms4
  • PetsYes

    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)

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


for 7 nights £670

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Delightful conversion of old cow byre in centre of Wrelton. Exposed timbers, wooden floors. Quality cottage, very high standard. Excellent walking and touring base. Pickering 3 miles. (Ref. 1577)

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


for 7 nights £287

  • 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 £492

  • 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


for 7 nights £375

  • 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 £356

Last booked 2 days ago
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  • Sleeps15
  • Bedrooms6
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Immaculately-presented period property in Amotherby village. Beautiful, spacious rooms, original features, open fires. High quality, antique furnishings. Lovely gardens. Pub 3 mins walk, Malton market town 3 miles. (Ref. 15823)

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


for 7 nights £1806

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Spring Cottage is a delightful cottage located in the scenic village of Husthwaite, near Easingwold in North Yorkshire, well-positioned to an array of attractions. York 17.8 miles; Harrogate 22.2 miles. (Ref. 1174191)

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


for 7 nights £498

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • 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
  • Washing machine
  • 10% off - Fri 6th Feb to 3rd Apr 2026


for 7 nights £673

  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

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


for 7 nights £448

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    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)

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


for 7 nights £477

  • 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 £295

  • 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

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

6 Fairfax Close, a lovely bungalow located in the village of Ampleforth in North Yorkshire. Single-storey. Enclosed garden. Off-road parking. Smart TV. Helmsley 5.3 miles; York 19.3 miles; Scarborough 35.8 miles. (Ref. 1159135)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly


for 7 nights £485

  • Sleeps6
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights £581

  • 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 yesterday
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