Cottages in Helmsley

Your Helmsley, North Yorkshire search returned 118 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
  • PetsNo

    5.0

    Perfect

  • 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


for 7 nights £406

  • 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


for 7 nights £319

Last booked yesterday
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  • 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
  • 10% off - Fri 24th Jul to 31st Jul 2026

  • 10% off - Fri 7th Aug to 14th Aug 2026


for 7 nights £392

Last booked 2 days ago
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  • Sleeps15
  • Bedrooms6
  • PetsYes

    4.8

    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)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Wed 22nd Apr to 31st Jul 2026

  • £1913 off - Mon 17th Aug to 24th Aug 2026

  • £1885 off - Sun 30th Aug to 6th Sep 2026


for 7 nights £1806

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Single-storey stone barn conversion set on owner's working farm, between Thirsk and Easingwold. Spacious open plan living area, woodburner. Two bedrooms, two bathrooms. High standard throughout. Excellent walking, cycling, touring. Easingwold 5 miles. (Ref. 930756)

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


for 7 nights £500

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    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 £484

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A charming ground floor annexe resting in Yearsley, North Yorkshire. Open-plan living. Malton 13.4 miles; York 16 miles. (Ref. 1022390)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • 10% off - Fri 1st May to 30th Jun 2026


for 7 nights £470

  • 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 £353

  • 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

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A welcoming, detached lodge resting in Cropton near Middleton, North Yorkshire. Ground-floor living. Pet-friendly. Off-road parking. Aislaby 2.8 miles; Pickering 5.2 miles; York 30.6 miles. (Ref. 1003270)

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


for 7 nights £603

  • 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
  • 5% off - Thu 30th Apr to 1st Jun 2026


for 7 nights £462

  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Detached stone barn conversion in courtyard setting on owners' farm, near Kirkbymoorside. Single-storey accommodation, with a comfortable open plan living area and pretty bedroom. Easy access to North York Moors National Park. Kirkbymoorside 2.5 miles. (Ref. 929845)

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


for 7 nights £320

  • 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 £562

Last booked yesterday
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  • 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


for 7 nights £461

  • 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


for 7 nights £670

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Grade II listed, semi-detached, former coaching inn, near centre of Wrelton village. Full of character, exposed beams and woodburning stove. Pickering 3 miles. (Ref. 1844)

  • Wi-fi
  • Washing machine


for 7 nights £295

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Delightful stone cottage in courtyard, set in open countryside. Character, quality accommodation. Oak floors, exposed beams. Kirkbymoorside 1.5 miles, Pickering 6 miles. (Ref. 929319)

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


for 7 nights £579

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.2

    Good

  • Sykes rating

Charming, stone, period cottage in pretty village of Hutton-le-Hole. Open fire, cosy, comfortable accommodation. Private rear garden, lovely views over village green. Walkers' delight. Kirkbymoorside 3.5 miles. (Ref. 22745)

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


for 7 nights £453