24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Cottages in Helmsley

REFINE SEARCH

Your Helmsley, North Yorkshire search returned 154 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This terraced, stone cottage is located in Kirkbymoorside, North Yorkshire. Gas fire. Courtyard garden. Pickering 6 miles; Helmsley 5 miles. (Ref. 1007219)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $589

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    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 $392

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    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 $475

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    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 $557

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    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

7 nights from $456

  • 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 $435

  • Sleeps2
  • Bedrooms1
  • PetsYes

    3.9

    Good

  • Sykes rating

A cute, one-bedroom farm cottage resting in Fadmoor, North Yorkshire. Open-plan living. Romantic. Shared garden. Kirkbymoorside 2.8 miles; Helmsley 7.8 miles; Pickering 10.3 miles. (Ref. 1123588)

  • Wi-fi

7 nights from $406

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This charming semi-detached cottage is situated in the village of Stonegrave, in North Yorkshire. WiFi. En-suite. Woodburner. (Ref. 989054)

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

7 nights from $596

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    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

7 nights from $586

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

Cliff Cottage is a beautiful detached property in Boltby near Thirsk, North Yorkshire. Woodburning stove. In national park. Thirsk 5.4 miles; Northallerton 10.3 miles. (Ref. 1143122)

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

7 nights from $886

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    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

7 nights from $570

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • 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 $387

Last booked yesterday
See more details
  • Sleeps3
  • Bedrooms1
  • PetsYes

    4.9

    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 $429

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

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

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 $590

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

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

7 nights from $694

  • 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

7 nights from $371

Last booked 2 days ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    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

7 nights from $782

  • 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 $761

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A delightful detached single-storey cottage nestled in the quaint North Yorkshire village of Harome, near to Helmsley. WiFi. Romantic. Off-road parking. Garden. Kirkbymoorside 4.9 miles; Pickering 12 miles; Thirsk 16.8 miles; York 22.2 miles. (Ref. 1077779)

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

7 nights from $816

  • 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 $866