Cottages in Helmsley

Your Helmsley, North Yorkshire search returned 120 cottages

REFINE SEARCH
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

How reviews work

A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

3 Valley View Lodges is a detached, single-storey lodge resting in Nawton near Helmsley, North Yorkshire, boasting an electric fire and rural views. Kirkbymoorside 3.1 miles; Pickering 10.5; Thirsk 17 miles; York 24 miles. (Ref. 1077224)

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


for 7 nights From €415

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

Angram Cottage is a gorgeous abode set in the countryside of Angram Grange near Thirsk, North Yorkshire, near the pretty North York Moors National Park. North York Moors National Park 6.1 miles; Northallerton 15.1 miles; York 20.2 miles. (Ref. 1172363)

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


for 7 nights From €826

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Pretty, detached, ground floor stone cottage in a small hamlet near Helmsley. Cosy, characterful accommodation for couples. WiFi. Pretty garden. Superb walking country. Helmsley 2 miles. (Ref. 917006)

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


for 7 nights From €386

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.4

    Good

  • Sykes rating

Harwood Cottage, a stunningly-presented holiday home in the charming village of Hovingham. Streamside. Garden with barbecue. Conservatory. Child-friendly. Helmsley 7.9 miles; Malton 8.2 miles; York 17.3 miles. (Ref. 1155772)

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


for 7 nights From €902

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From €475

  • 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 €657

  • 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 €361

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    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 From €373

  • 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 €526

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

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


for 7 nights From €346

  • 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 €632

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Daisy Cottage is a charming holiday home in Pickering, North Yorkshire, with WiFi, private parking, and a welcoming interior. Scarborough 18.4 miles; Whitby 22.3 miles; York 26.4 miles. (Ref. 1190307)

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


for 7 nights From €461

  • 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 €420

Last booked 2 days ago
See more details
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Tourist Board rating

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

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Wed 24th Jun to 7th Aug 2026


for 7 nights From €409

  • 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 €370

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    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)

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


for 7 nights From €503

Last booked 2 days ago
See more details
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.0

    Good

  • Sykes rating

Holly Cottage is a stunning thatched dwelling sitting pretty in the village of Harome near Beadlam in North Yorkshire, enjoying a woodburning stove. Helmsley 2.7 miles; Pickering 12.3 miles; York 22.5 miles. (Ref. 1069742)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From €774

Last booked 2 days ago
See more details
  • Sleeps4
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Annex at Manor Farm is a lovely pet-friendly property near Brandsby, North Yorkshire, with an open-plan living space, an EV charger and a freestanding bath. York 16 miles. (Ref. 1182017)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging


for 7 nights From €427

  • 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 €408

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

A pretty cottage nestled in the picturesque village of Rosedale, North Yorkshire. Woodburning stove. Garden. Dishwasher. Kirkbymoorside 7.9 miles; Pickering 10.3 miles. (Ref. 1102061)

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


for 7 nights From €684