#{ServerName}

Helmsley cottages

Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)
Webstone Cottage (G0172)

Webstone Cottage

Osmotherley, North Yorkshire

4
2
1
pets 2

This charming cottage with an abundance of character in the North York Moors is an idyllic retreat for families looking to explore the natural treasures in the surrounding countryside.

Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)
Coco (G0037)

Coco

Helmsley, North Yorkshire

4
2
1
pets 1

A delightful haven on the fringes of the incredible North York Moors, offering friends and family a dreamy escape from the rhythm of everyday life.

St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)
St Aidans (G0131)

St Aidans

Helmsley, North Yorkshire

4
2
2
pets 2

This imaginatively converted Grade II listed former church offers cosy, welcoming and unique accommodation for couples looking for a lovely retreat on the outskirts of the beautiful North York Moors.

Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)
Hare House (G0072)

Hare House

Stokesley (2mls SW), North Yorkshire

4
2
1
pets 2

Gorgeous holiday home surrounded by the open countryside, situated on the cusp of the North York Moors National Park, equidistant to quaint villages and vibrant market towns offering attractions aplenty.

Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)
Partridge Cottage - Chopgate (G0108)

Partridge Cottage - Chopgate

Osmotherley, North Yorkshire

4
2
2
pets 2

Sympathetically converted to retain original brickwork and wooden beams, this rural barn conversion is a stylish bolthole for long walks over the moors.

 

 

 

Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)
Woodland View (77831)

Woodland View

Helmsley, North Yorkshire

4
2
2
Explore the gems of North Yorkshire and its stunning beaches and coastline walks, an ideal base for Family or friends wishing to explore the Yorkshire countryside.
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)
Isla Cottage (77528)

Isla Cottage

Osmotherley, North Yorkshire

4
2
1
pets 1
Snug and inviting, this pretty retreat is well-suited for couples or small families wishing to spend some time away from it all in a picturesque rural location on the edge of the North York Moors.
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)
Pheasant Cottage - Chopgate (G0110)

Pheasant Cottage - Chopgate

Osmotherley, North Yorkshire

6
3
2
pets 2

The larger of two barn conversions, this beautiful property is perfect for memorable getaways in the North York Moors.

Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)
Rose Cottage - Helmsley (G0118)

Rose Cottage - Helmsley

Helmsley, North Yorkshire

6
3
3

Beautifully finished throughout, this modern townhouse is the perfect venue for special celebrations with friends or family in popular Helmsley.

The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)
The Old Hay Barn (77667)

The Old Hay Barn

Great Busby, North Yorkshire

6
3
1
pets 2
Enjoy relaxing in this countryside retreat on the cusp of the North York Moors. The open-plan space provides the ultimate social accommodation to take a relaxing break with friends or family.
One Ryegate (79527)
One Ryegate (79527)
One Ryegate (79527)
One Ryegate (79527)
One Ryegate (79527)
One Ryegate (79527)
One Ryegate (79527)

One Ryegate

Helmsley, North Yorkshire

6
3
2
pets 1
With a plethora of places to visit and activities to experience, you are spoilt for choice when it comes to stays in Helmsley. Ideal village centre location for keen walkers, thrill seekers and nature lovers.
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)
Tawny Owl Cottage (74582)

Tawny Owl Cottage

Carlton-in-Cleveland, North Yorkshire

6
3
2
pets 2

Escape to this cosy cottage and embrace adventure by exploring the North York Moors, an Area of Outstanding Natural Beauty, the perfect base to enjoy wide open space or stay in, with the private enclosed garden or relax and snuggle up in front of the wood burner.

Self-catering holiday accommodation in Helmsley

Stay in a luxury holiday home in Helmsley on your getaway to Yorkshire. Helmsley is a traditional English market town with a stately square, castle ruins, enticing cafes and tea rooms, and old-fashioned pubs where you can drink local ales from tankards. Two major walking trails originate in Helmsley: The Cleveland Way and the Ebor Way.  Bring your walking boots and enjoy mile-upon-mile of staggeringly beautiful North Yorkshire countryside. Your dog will enjoy these walking routes too, and we have a great range of dog-friendly properties to choose from too. Best of all are the ruins of Helmsley’s wonderful castle; towering over the town the crumbling edifice is now managed by English Heritage. You can still marvel at the keep, cleaved in two during a three-month siege by Oliver Cromwell’s men. Also head to Helmsley’s walled garden if you love flowers, plants and peace and quiet.

Local highlights in the wider area also include: Castle Howard, which enjoys popular connections to the phenomenally famous TV show Downton Abbey; stalk the Bronte sisters around Haworth and the moors that inspired their spellbinding stories; or head over to Hawes to sample some Wensleydale Cheese. The quiet ruins of Rievaulx Abbey are also unmissable during your trip to Helmsley and the surrounding area.

Search
nights
+ / - days
guests
bedrooms
dogs
Filters

Location

  • Pub within 1 mile
  • Waterside views
  • Shop within 1 mile
  • Beach within 5 miles

Facilities

  • Games / Play facilities
  • Hot tub
  • Enclosed garden / patio
  • Four poster bed
  • Sky TV
  • Swimming pool
  • Indoor swimming pool
  • Open fire / woodburner
  • Tennis court
  • Spa facilities
  • Internet access

Property

  • Log cabin / Lodge
  • Working farm
  • Downstairs bedroom
  • Romantic
  • Family friendly
  • Increased accessibility
  • Quirky
  • Does not allow pets
  • Downstairs bathroom
  • Shepherd hut
  • Luxury
  • Apartment
The Travel Chapter Limited, trading as holidaycottages.co.uk | The Travel Chapter Limited is registered in England and Wales. | Registered office Travel Chapter House Gammaton Road Bideford EX39 4DF Company No. 02431506 | VAT reg: 143053210