Cottages in Helmsley

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

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Games room


for 7 nights From $421

Holiday Park

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    3.5

    Good

  • 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)

  • Pet friendly (extra charges may apply)
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • $34 off - Wed 19th Aug to 30th Nov 2026


for 7 nights From $1040

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    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)

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


for 7 nights From $735

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Delightful brick-built Stillington cottage on edge of pretty village. Tastefully renovated with comfortable accommodation. Excellent walking nearby. Close to many attractions. York 11 miles. (Ref. 4458)

  • Off-road parking
  • Washing machine
  • Baby-friendly


for 7 nights From $481

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

This inviting mid-terrace sits at the centre of Pickering in North Yorkshire, on the fringes of the North York Moors National Park. Three-storey. Pet-friendly. Amenities in walking distance. Malton 8.7 miles; Scarborough 18.2 miles; York 26.8 miles. (Ref. 1025071)

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


for 7 nights From $489

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.3

    Good

  • 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 From $455

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    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 From $597

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

Converted barn on a working farm, 3.5 miles from Kirkbymoorside in North Yorkshire. All ground floor. Open-plan. Exposed beams. Countryside views. (Ref. 974387)

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


for 7 nights From $480

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    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 From $628

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.8

    Outstanding

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

Superb Rosedale Abbey cottage, a conversion of a Victorian chapel with lovely views. Character features, accommodation over four floors, wonderful year-round base. Kirkbymoorside 7 miles. (Ref. 8233)

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


for 7 nights From $779

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From $410

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • 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 From $693

  • Sleeps15
  • Bedrooms6
  • Pet FriendlyYes

    4.9

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Tue 1st Sep to 30th Sep 2026


for 7 nights From $2361

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Beautiful stone cottage in the North York Moors National Park, close to the village of Hutton-le-Hole. Exposed beams. Surrounded by countryside. Hutton-le-Hole 1.5 miles. (Ref. 975266)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights From $431

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    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 From $485

  • 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 $534