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 144 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

    4.9

    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 £476

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

    4.9

    Sykes Rating

A lovely converted carriage house dating back to the 18th century in the village centre of Ampleforth, North York Moors National Park. Underfloor heating. Woodburning stove. Village centre. Helmsley 4.9 miles; Rievaulx 7.5 miles; Kirkham Abbey 17.3 miles. (Ref. 1051110)

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

7 nights from £587

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    Sykes Rating

Badger is an elegant house in Little Thirkleby, North Yorkshire, boasting an enclosed garden, and access to a tennis court, swimming pool. Ripon 15.5 miles; Helmsley 12.2 miles; York 21 miles. (Ref. 1170004)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Washing machine
  • Baby-friendly

7 nights from £1036

7 nights from £487

  • 8 Guests
  • 4 Bedrooms
  • Pets No

    4.9

    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 £674

  • 6 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    Sykes Rating

Temple Hill View, a friendly abode in the village of Ampleforth in North Yorkshire. Off-road parking. Near shop. Enclosed garden. Countryside views. Helmsley 5.1 miles; York 19.3 miles; Scarborough 35.6 miles. (Ref. 1159134)

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

7 nights from £532

  • 8 Guests
  • 4 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

Magnificent semi-detached property in market town of Helmsley. Beautifully presented and well-equipped. Open fire, conservatory, delightful garden. Close to all amenities. (Ref. 2779)

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

7 nights from £839

  • 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

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    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
  • Baby-friendly

7 nights from £417

  • 2 Guests
  • 1 Bedroom
  • Pets No

    5.0

    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 £350

  • 4 Guests
  • 2 Bedrooms
  • Pets No

    5.0

    Sykes Rating

A lovely, two-bedroom cottage resting in Kirkbymoorside, North Yorkshire. Near National Park. Countryside views. Close to amenities. Contemporary. Ground-floor living. Enclosed garden. Helmsley 6.1 miles; Pickering 7.6 miles. (Ref. 1131837)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £363

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.6

    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 £578

  • 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

  • 5 Guests
  • 3 Bedrooms
  • Pets Yes

    5.0

    Sykes Rating

A superb, detached lodge resting on the outskirts of Kirkbymoorside. All-ground-floor. WiFi. Pet-friendly. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011649)

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

7 nights from £479

  • 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

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    5.0

    Sykes Rating

The Burrows, a charming holiday cottage located in the quaint town of Helmsley, North Yorkshire. Woodburning stove. Enclosed garden. In North York Moors.Helmsley 6.4 miles; York 21.3 miles; Scarborough 38 miles. (Ref. 1150998)

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

7 nights from £506

  • 5 Guests
  • 3 Bedrooms
  • Pets Yes

    4.9

    Sykes Rating

A wood-clad lodge resting within the town of Kirkbymoorside. All-ground-floor. Pet-friendly. WiFi. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011653)

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

7 nights from £479

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

    4.7

    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
  • 10% off - Sat 1st Mar to 2nd May 2025

7 nights from £1764

  • 6 Guests
  • 3 Bedrooms
  • Pets No

    4.2

    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

7 nights from £523

  • 5 Guests
  • 3 Bedrooms
  • Pets No

    4.7

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 £496

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.