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Helmsley holiday cottages

48 properties found
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
Ferne Cottage - Helmsley (81052)
NEW

Ferne Cottage - Helmsley

Helmsley, North Yorkshire

3
2
1
pets 1
A delightful, bijou holiday cottage tucked away in a quiet location in Helmsley, one of the prettiest and most visited market towns in Yorkshire. Perfect for small families
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

3
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.

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

3
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.
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.

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 (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.

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.
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.

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.

Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)
Grange View Cottage - Thirsk (87460)

Grange View Cottage - Thirsk

Thirsk, North Yorkshire

4
2
1
pets 2
Discover this delightful cottage located in the tranquil village of South Kilvington, between two Yorkshire National Parks, this is an excellent retreat for countryside lovers, keen walkers and cyclists
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)
Lavender Cottage - Helmsley (82891)

Lavender Cottage - Helmsley

Helmsley, North Yorkshire

5
3
1
pets 1
This charming cottage set within the traditional market town of Helmsley is brimming with character and is perfect for a family of walkers wanting to explore the North York Moors National Park.
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.

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.

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 tearooms, and old-fashioned pubs where you can drink local ales from tankards. The only market town in the North York Moors National Park, our holiday cottages in Helmsley offer the perfect base for outdoor adventures, but there’s also plenty of things to do in Helmsley right from your front door.

Helmsley has a reputation as being a creative town, home to the Helmsley Arts Centre which hosts a fine selection of pantomimes, films, dance, theatre, art workshops and events throughout the year. And on a warm, sunny day, nothing beats a refreshing dip in Helmsley’s Open Air Swimming Pool, which is open from June until September.

A luxury Helmsley staycation

A stay in one of our Helmsley luxury holiday cottages is guaranteed to delight couples and families alike, as there is plenty to enchant keen walkers, budding historians and leisure seekers throughout this fantastic location. We have dog-friendly Helmsley cottages so your best friend can come along too or browse our full range of North Yorkshire cottages to discover even more market towns and pretty villages.

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Filters

Location

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

Facilities

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

Minimum star grading

Property

  • Luxury
  • Quirky
  • Log cabin / Lodge
  • Downstairs bathroom
  • Does not allow pets
  • Apartment
  • Working farm
  • Increased accessibility
  • Romantic
  • Family friendly
  • Shepherd hut
  • Downstairs bedroom

Recently added

  • Added in last 2 months
The Travel Chapter Limited trading as Gorgeous Cottages is an appointed representative of ITC Compliance Limited which is authorised and regulated by the Financial Conduct Authority (their registration number is 313486) and which is permitted to advise on and arrange general insurance contracts as an intermediary.
The Travel Chapter Limited trading as Gorgeous Cottages | 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.