Cottages in Helmsley

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Your Helmsley, North Yorkshire search returned 140 cottages

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  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Beautiful, first floor, studio-style cottage in rural location. Close to Easingwold and Crayke. Tastefully furnished to high standard. Woodburner, splendid views. Easy access to York. Easingwold 2 miles. (Ref. 917511)

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

7 nights from £313

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This delightful detached house is situated in Sinnington, North Yorkshire. WiFi, Pet-friendly, Off-road parking. Pickering 3 miles; Kirkbymoorside 3.5 miles. (Ref. 998951)

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

7 nights from £607

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stunning ground floor barn conversion five miles from Malton in North Yorkshire. Open-plan living. En-suites. Countryside views. Near North York Moors National Park. (Ref. 943576)

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

7 nights from £532

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A luxury, detached, stone barn conversion in Sutton-under-Whitestonecliffe near Thirsk, North Yorkshire. Woodburning stove. Pool table. Large shared garden. Thirsk 4.6 miles; Northallerton 12.7 miles. (Ref. 1052313)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £464

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This quaint cottage lies in the market town, Hemlsley, North Yorkshire. Original features. WiFi. Off-road parking. Kirkbymoorside 6 miles; Pickering 13.1 miles; Thirsk 14.3 miles; York 24.8 miles. (Ref. 1064092)

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

7 nights from £578

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A characterful three bedroom holiday cottage settled in Helmsley, in North Yorkshire. Garden. Pet-friendly. Washing machine. Kirkbymoorside 6 miles; Pickering 13.1 miles; Thirsk 14 miles; York 24.1 miles. (Ref. 1089307)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £604

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

This rural detached cottage rests in Chop Gate, near Stokesley, in North Yorkshire. Stunning countryside views. Reverse-level layout. WiFi. Great Ayton 10.1 miles; Saltburn-by-the-Sea 20.5 miles. (Ref. 1025549)

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

7 nights from £656

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

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A charming barn conversion located near the village of Thirsk, North Yorkshire. Breakfast bar. Open-plan. High ceilings. Ripon 11 miles; York 23 miles. (Ref. 19934)

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

7 nights from £290

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A delightful three bed barn conversion on a small complex, in peaceful location on the edge of the village of Sutton-Under-Whitestonecliffe. Open plan living area, galleried landing. Ideal walking area. Thirsk 4 miles. (Ref. 19935)

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

7 nights from £487

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Immaculately-presented, single-storey stone barn conversion in small hamlet of Stearsby near York. Woodburning stove. Countryside views, close to pretty market towns of Helmsley, Easingwold. York 14 miles. (Ref. 8634)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 4th Jul to 31st Jul 2025

7 nights from £777

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This superb detached, stone barn conversion rests on the outskirts of Thirsk, North Yorkshire. Woodburner. Pet-friendly. Northallerton 12.7 miles. (Ref. 1021256)

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

7 nights from £463

  • Sleeps5
  • Bedrooms3
  • PetsYes

    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)

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

7 nights from £377

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Owl's Nest is a fabulous detached barn conversion offering flexible accommodation and beautifully positioned in the glorious Howardian Hills near York and Malton. York 12 miles. (Ref. 20946)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 11th Jul to 24th Jul 2025

7 nights from £580

  • Sleeps2
  • Bedrooms1
  • PetsYes

    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)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £343

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

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A charming barn conversion located near the village of Thirsk, North Yorkshire. Open-plan. Upside down living. Exposed stonework. Ripon 11 miles; York 23 miles. (Ref. 19936)

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

7 nights from £437

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Exceedingly pretty, detached stone cottage, a short walk from centre of Kirkbymoorside. Beamed ceilings, open fire. National Park and Heritage Coast within easy driving distance. Pickering 6 miles. (Ref. 1034138)

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

7 nights from £411

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A stone-built cottage which rests on the outskirts of Thirsk, North Yorkshire. Open-plan. WiFi. Just a moment’s walk from the Cleveland National Trail. York 27 miles. (Ref. 1004365)

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

7 nights from £296

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Detached stone built stable conversion in pretty Lastingham village. Quality ground floor accommodation, streamside patio. Ideal for York Moors & Coast. Pickering 7 miles. (Ref. 1293)

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

7 nights from £361

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming, Grade II listed cottage on the edge of pretty Kirkbymoorside, Yorkshire. Pickering 6 miles. Close to North York Moors National Park. (Ref. 985142)

  • Wi-fi
  • Washing machine

7 nights from £395

  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.8

    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 £456