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 117 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
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Charming detached stone-built barn conversion in picturesque Lastingham. Quality accommodation with woodburning stove. Excellent walking, coast easily accessible. Pickering 7 miles. (Ref. 1571)

  • Wi-fi
  • Off-road parking

7 nights from £351

Last booked yesterday
See more details
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

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

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 £441

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A characterful two-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 £472

Last booked 3 hours ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5

    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 £553

  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

A charming barn conversion resting in Stearsby near Stillington, North Yorkshire. Near National Park. Countryside views. Rural. Contemporary. Woodburning stove. Romantic. Easingwold 6.4 miles; Helmsley 10.8 miles; Malton 13.8 miles; York 14.5 miles. (Ref. 1150298)

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

7 nights from £743

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    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 £476

  • 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 £703

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

7 nights from £990

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Ideal for a family holiday in the heart of market town. Front garden and rear courtyard. WiFi. Thirsk 14 miles. (Ref. 956799)

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

7 nights from £581

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A charming, stone-built cottage resting on the outskirts of Helmsley. Pet-friendly. WiFi. Woodburning stove. Kirkbymoorside 5.3 miles. (Ref. 1016619)

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

7 nights from £313

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A romantic, single-storey cottage resting in Beadlam, North Yorkshire. Open-plan. Beautiful views. Helmsley 2.2 miles; Pickering 10.9 miles; York 24.4 miles. (Ref. 1099725)

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

7 nights from £401

Last booked 2 days ago
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo
  • 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
  • £114 off - Fri 3rd May to 10th May 2024

  • £169 off - Fri 24th May to 31st May 2024

  • 20% off - Fri 31st May to 7th Jun 2024

  • £119 off - Fri 21st Jun to 28th Jun 2024

  • £134 off - Fri 28th Jun to 5th Jul 2024

  • £99 off - Fri 5th Jul to 12th Jul 2024

  • £194 off - Fri 26th Jul to 2nd Aug 2024

7 nights from £478

Last booked 8 hours ago
See more details
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Beautiful period property in village location. Ensuite bathroom. TV with Freeview. Lovely garden. Ample off road parking. Village location with pub and restaurant. Helmsley 3 miles. (Ref. 943848)

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

7 nights from £654

  • 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 £292

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    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 £353

  • 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 £383

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A wonderful, semi-detached cottage settled in Stonegrave near Hovingham, North Yorkshire. Woodburning stove. Near National Park. Romantic. Helmsley 5.9 miles; Malton 10.1 miles; York 18.5 miles. (Ref. 1106690)

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

7 nights from £343

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

    4.9

    Outstanding

  • Sykes rating

A wonderful stone bungalow located in the village of Gillamoor, North Yorkshire. Open-plan. Woodburner. Open countryside views. Kirkbymoorside 2.7 miles; Pickering 11 miles. (Ref. 984261)

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

7 nights from £453

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

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

Cosy town house in heart of Kirkbymoorside. Three storeys, welcoming accommodation. Convenient location, good base for moors, coast, York and more. (Ref. 17787)

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

7 nights from £608

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • 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. 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 £281

On the border of the North York Moors National Park, this delightful market town is a haven for walkers and lovers of the outdoors.

Why Helmsley?

After an action-packed day among the wonders of the North York Moors, our Helmsley cottages enjoy close proximity to the town's charming pubs and delightful tea rooms to recharge the batteries. There is a selection of excellent independent shops and a weekly market along its attractive streets to pick up some of the finest local produce. From your Helmsley accommodation, be sure to explore the stunning Helmsley Castle and sculpture garden, as well as Duncombe Park and the National Centre for Birds of Prey for nature enthusiasts.

Places to Visit near Helmsley

Our range of cottages in Helmsley rest on the southern fringes of the North York Moors National Park, perfectly based for a break filled with activity and adventure. This National Park hugging the coast of Yorkshire has much to offer, not least its wide range of walks and cycle paths taking in some of the finest landscape scenery imaginable. Discover a handful of unique villages in and around the spectacular moors, waiting to be explored with rustic inns and delightful cafés offering those mid-adventure refreshments. Make your Helmsley cottage holiday a memorable one by visiting popular spots such as Ampleforth, Hutton-le-Hole, Kirkbymoorside, Pickering, Ripon and Thirsk.

Types of Holidays

All types of holidays can be enjoyed across Yorkshire with Sykes, whether you're seeking a Yorkshire cottage by the sea, or more of a rural retreat at a cottage in the Yorkshire countryside. Bring your dog along to enjoy the sublime walking country nearby by booking a North York Moors pet-friendly cottage, or really treat yourselves to a break in a Yorkshire luxury cottage.