Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 119 cottages

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  • 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 €420

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

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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 €427

Last booked yesterday
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  • Sleeps4
  • Bedrooms1
  • PetsYes
  • Sykes rating

The Annex at Manor Farm is a lovely pet-friendly property near Brandsby, North Yorkshire, with an open-plan living space, an EV charger and a freestanding bath. York 16 miles. (Ref. 1182017)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging


for 7 nights €434

  • Sleeps5
  • Bedrooms2
  • PetsNo
  • Sykes rating

Low Muffles Bridge is a single-storey cottage tucked away in the peaceful hamlet of Hartoft in North Yorkshire, complete with a handy utility. Whitby 20.7 miles; Scarborough 26.2 miles; York 34.2 miles. (Ref. 1176206)

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


for 7 nights €463

  • 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 €506

Last booked 2 days ago
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  • 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 €624

  • 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 €910

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1

    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


for 7 nights €544

  • 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 €1100

  • 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 €465

  • 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 €408

  • 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 €751

Holiday Park

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Isca Lodge – with Decking, a neat single-storey lodge near Wombleton and North York Moors National Park, boasts a private deck and open-plan design. Kirkbymoorside 3.9 miles; Helmsley 4.3 miles; Pickering 10.8 miles. (Ref. 1191239)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • 25% off - Fri 21st Nov 2025 to 20th Mar 2026


for 7 nights €627

  • 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 €1117

  • 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 €453

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo
  • Sykes rating

St. Anthonys is a lovely house resting in Ampleforth, North Yorkshire, featuring three bedrooms, a woodburning stove, and a garden for alfresco dining. Helmsley 4.6 miles; York 26.3 miles; Scarborough 35.2 miles. (Ref. 1196483)

  • Wi-fi
  • Off-road parking


for 7 nights €624

  • 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 €481

Holiday Park

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Isca Lodge is a stylish single-storey lodge near Wombleton, North Yorkshire, offering an open-plan layout and access to the North York Moors National Park. Kirkbymoorside 3.9 miles; Helmsley 4.3 miles; Pickering 10.8 miles. (Ref. 1191241)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • 25% off - Fri 21st Nov 2025 to 20th Mar 2026


for 7 nights €610

Holiday Park

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Rye Lodge, a plush lodge resting near Wombleton, North Yorkshire, with open-plan living, a freestanding bath and is near to North York Moors National Park. Kirkbymoorside 3.9 miles; Helmsley 4.3 miles; Pickering 10.8 miles. (Ref. 1191243)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • 25% off - Fri 21st Nov 2025 to 20th Mar 2026


for 7 nights €610