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 143 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
  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    5.0

    Sykes Rating

Cosy character cottage in wonderful rural position. All ground floor with disability rating. Views over open countryside. Kirkbymoorside 1.5 miles; Pickering 6 miles. (Ref. 929318)

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

7 nights from £577

Last booked yesterday
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

Lilac Cottage is a delightful cottage nestled in the village of Wombleton in North Yorkshire. Close to farm shop. Near North York Moors. Enclosed garden. Helmsley 4.2 miles; Pickering 10.1 miles; York 22.2 miles (Ref. 1126412)

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

7 nights from £366

Last booked 2 days ago
See more details

Travel plans can change

Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).

Find out more. T&Cs apply

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    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

Last booked 2 days ago
See more details
  • 4 Guests
  • 2 Bedrooms
  • Pets No

    5.0

    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
  • 10% off - Fri 4th Apr to 11th Apr 2025

7 nights from £496

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.9

    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

  • 5 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    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

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

This character detached lodge rests in Nawton near Helmsley, North Yorkshire. Beautiful views. Electric fire. Ground-floor living. WiFi. Off-road parking. Kirkbymoorside 3.1 miles; Pickering 10.5; Thirsk 17 miles; York 24 miles. (Ref. 1077224)

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

7 nights from £399

Last booked 2 days ago
See more details

Travel plans can change

Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).

Find out more. T&Cs apply

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    5.0

    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 £669

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.9

    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

7 nights from £401

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.8

    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

  • 4 Guests
  • 2 Bedrooms
  • Pets Yes

    4.8

    Sykes Rating

Cosy, ground floor cottage placed near the North Yorkshire town of Kirkbymoorside. Open-plan living. Exposed wooden beams. En-suites. Near North York Moors National Park. (Ref. 974388)

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

7 nights from £405

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    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

7 nights from £502

  • 5 Guests
  • 3 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A well-equipped bungalow situated in the market town of Pickering, Yorkshire. Ideal for families. Touring location. Kirkbymoorside 6.6 miles; Helmsley 12.1 miles. (Ref. 1070204)

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

7 nights from £499

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

Wonderful, semi-detached, barn conversion near Thirsk. Eco-friendly central heating. WiFi. Open plan living area. Ideal touring location. Thirsk 4 miles. (Ref. 15032)

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

7 nights from £356

Last booked yesterday
See more details

Travel plans can change

Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).

Find out more. T&Cs apply

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    4.9

    Sykes Rating

This beautifully appointed, semi-detached cottage rests in Marton near Kirkbymoorside, North Yorkshire. Ground-floor living. Off-road parking. Smart TV. Pet-free. Pickering 4.8 miles; Helmsley 9.1 miles; York 25.6 miles. (Ref. 1102616)

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

7 nights from £474

  • 2 Guests
  • 1 Bedroom
  • Pets No

    4.9

    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

Last booked 5 hours ago
See more details
  • 10 Guests
  • 5 Bedrooms
  • Pets No

    4.5

    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 £1008

7 nights from £396

Last booked yesterday
See more details
  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

Superb barn conversion in open countryside 1.5 miles from Kirkbymoorside. Beams, exposed stone work, woodburning stove. Pickering 6 miles. (Ref. 929317)

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

7 nights from £636

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.9

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 £481