Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 150 cottages

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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

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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

7 nights from $670

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

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

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

7 nights from $484

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Bay Tree Cottage is a delightful terraced cottage resting in Pickering, North Yorkshire. Near National Park. Woodburning stove. Close to shop and pub. Kirkby Misperton 4.4 miles; Malton 8.8 miles. (Ref. 1115722)

  • Wi-fi
  • Dishwasher
  • 5% off - Fri 14th Nov to 21st Nov 2025

  • 5% off - Fri 28th Nov to 5th Dec 2025

7 nights from $575

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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)

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

7 nights from $477

  • 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

7 nights from $886

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  • 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

7 nights from $602

  • 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

7 nights from $709

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Detached pet-friendly cottage near Hovingham. Single-storey cottage, rural position on arable farm estate, underfloor heating. Well equipped and comfortable. Close to Nunnington, Castle Howard, pretty market towns. Hovingham 3 miles. (Ref. 21723)

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

7 nights from $409

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A characterful barn conversion resting on a working farm near the town of Kirkbymoorside. TV with Freeview. Countryside views. Near North York Moors National Park. Dog-friendly. (Ref. 974385)

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

7 nights from $431

  • Sleeps10
  • Bedrooms5
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A charming stone-fronted cottage resting in Ampleforth, North Yorkshire. Original features. In North York Moors National Park. Close to amenities. Woodburning stove. Helmsley 4.9 miles; York 19.4 miles; Scarborough 35.4 miles. (Ref. 1115609)

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

7 nights from $1206

  • Sleeps4
  • Bedrooms2
  • PetsNo

    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

7 nights from $476

  • 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

7 nights from $638

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A well-presented barn conversion, on a working farm and close to the Yorkshire town of Kirkbymoorside. Open-plan living. En-suite. Near North York Moors National Park. Pet-friendly. (Ref. 974386)

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

7 nights from $431

  • 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

7 nights from $418

  • 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

7 nights from $431

  • 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

7 nights from $520

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A delightful, semi-detached bungalow resting in the pretty village of Harome in North Yorkshire. Ideal for two couples. Enclosed lawned garden. Helmsley 3 miles; Pickering 11.6 miles. (Ref. 1044119)

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

7 nights from $690

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Green is a detached cottage located in the village of Lastingham near Kirkbymoorside, North Yorkshire. Child-friendly. Woodburning stove. Countryside views. Kirkbymoorside 5.3 miles; Pickering 9.2 miles. (Ref. 1134717)

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

7 nights from $998

  • 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

7 nights from $673

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.8

    Outstanding

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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

7 nights from $621