Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 153 cottages

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  • 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 £504

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Lovely double-fronted cottage within a short stroll of the picturesque market town of Helmsley within the North Yorkshire National Park. WiFi. Lawned garden. Walks from the door. Kirkbymoorside 6 miles. (Ref. 947064)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights £491

  • 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 £403

  • 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

  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A delightful mid-terrace cottage resting within the market town of Pickering. Woodburning fire. Fibre Optic WiFi. Pub within 0.2 miles. Scarborough 18 miles; Whitby 22 miles. (Ref. 1003948)

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


for 7 nights £450

  • 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 £370

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Magnificent semi-detached barn conversion in Farndale. Full of character and charm, exposed beams and open fire. Excellent walking from the doorstep. Kirkbymoorside 10 miles. (Ref. 1391)

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


for 7 nights £462

  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

The Burrows, a charming holiday cottage located in the quaint town of Helmsley, North Yorkshire. Woodburning stove. Enclosed garden. In North York Moors.Helmsley 6.4 miles; York 21.3 miles; Scarborough 38 miles. (Ref. 1150998)

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


for 7 nights £554

  • 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 £520

Last booked 2 days ago
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  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Detached attractive stone barn conversion in a peaceful location near Kirkbymoorside. Single-storey accommodation with exceptional countryside views and superb walking opportunities. Kirkbymoorside 2.5 miles. (Ref. 911836)

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


for 7 nights £310

  • 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 £552

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 £555

  • 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 £371

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Honeysuckle Cottage is a holiday cottage situated in the pleasant little village of Oswaldkirk near Helmsley in North Yorkshire, with a woodburning stove. Kirkbymoorside 9.9 miles; Thirsk 14.7 miles; Pickering 16.8 miles; York 20.8 miles. (Ref. 1174608)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Tue 2nd Dec to 21st Dec 2025

  • 15% off - Mon 22nd Dec 2025 to 4th Jan 2026


for 7 nights £399

  • Sleeps4
  • Bedrooms2
  • PetsNo

    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 £354

  • 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
  • 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 £365

Last booked yesterday
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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 £530

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 £530

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Delightful semi-detached barn conversion in Farndale, 2 miles from Low Mills. Fabulous farmhouse kitchen with open fire. Excellent walking and cycling nearby. Kirkbymoorside 10 miles. (Ref. 1392)

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


for 7 nights £584